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This is an old revision of this page, as edited by Rhetro29 (talk | contribs) at 17:04, 13 February 2006 (→Stille reaction). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

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Torsional Strain

V8rik, can you write a page on torsional strain for wiki? There is one for angular strain, but when you go to torsional strain, wikipedia redirects you to eclipsed.

For now Torsional_strain redirects to Alkane stereochemistry V8rik 23:15, 2 January 2006 (UTC)[reply]

Thanks

Hi,

Thanks for starting a page on convergent synthesis, it's much needed, as well as the many other contributions you've made on other topics in organic chemistry. We need as many chemists as we can get on Wikipedia, we have been pretty short of people in this area. Although I see you're fairly new, you seem to have found your way around pretty well- though I'm still finding things after six months on Wikipedia. In case you haven't found them yet, some of the useful pages on chemistry topics are:

Thanks again, Walkerma 14:55, 7 Apr 2005 (UTC)

Hello again. I was taking a look at your new page on DABCO, and I notice that you're using an out-of-date table. Have you seen the options at Wikipedia:Chemical_infobox? I would recommend using Cacycle's table Template:Chembox_simple_organic, which is currently in use on over 150 organic compound pages. Meanwhile I have been adding your new compound pages into the lists. Thanks again, Walkerma 16:20, 22 Apr 2005 (UTC)

Ester

I noticed that you moved the content from ester to ester compound. I have made some comments about this on talk:ester. Overall i am not very happy with this. You should have called the page ester (chemistry) if he move was absolutely necesary.

Borb 08:31, 6 May 2005 (UTC)[reply]

I have to say that I agree with Borb on this- I have never heard esters called "ester compounds" before, and also the alternatives are so obscure compared to the importance of esters in chemistry. It is quite common to have several meanings- but if one dominates then it should take that name. See iron, copper and morphine. Walkerma 15:51, 6 May 2005 (UTC)[reply]

Image:TMP.gif

Image deletion warning The image Image:TMP.gif has been listed at Wikipedia:Possibly unfree images. If the image's copyright status cannot be verified, it will be deleted. If you have any information on the source or licensing of this image, please go there to provide the necessary information.

Burgundavia (✈ take a flight?) 01:02, May 13, 2005 (UTC) {{subst:idw-puiImage:TEMPO.gif|}} Burgundavia (✈ take a flight?) 01:02, May 13, 2005 (UTC)

Image:TMP synthesis.gif

Image deletion warning The image Image:TMP synthesis.gif has been listed at Wikipedia:Possibly unfree images. If the image's copyright status cannot be verified, it will be deleted. If you have any information on the source or licensing of this image, please go there to provide the necessary information.

Burgundavia (✈ take a flight?) 01:04, May 13, 2005 (UTC)

I agree, the current upload form sucks. However, that is what we have. Basically, we need two things. 1. A source (you in this case), you mention that you created it. 2. A licence. The GFDL is what the text is licenced under, but you can see more at Wikipedia:Copyrights. Cheers. Burgundavia (✈ take a flight?) 22:52, May 13, 2005 (UTC)

  • Hey, for all your images, you can remove the PUI and no source stuff, and add {{PD-self}} Cheers. Burgundavia (✈ take a flight?) 05:56, May 27, 2005 (UTC)

Thanks!

Hi! I'd just like to commend you for your contributions to the Wikipedia, especially in the area of chemistry. Good work! — flamingspinach | (talk) 22:42, 2005 May 26 (UTC)

Great job on the new maleic acid page! Thanks a lot, Walkerma 19:53, 11 July 2005 (UTC)[reply]

Bravo Zulu; Yet more thanks

You really improved the DMSP entry that I recently posted.

I never would have thought to make links to terms like abiotic and a couple of the others. I could blame it on working in this particular area for a while, but the whole idea of an entry is to convey useful information. Field-specific jargon gets in the way of that. Thanks again.

prokaryote 23:49, 6 Jun 2005 (UTC)

(note I've changed screen names since the DMSP entry. Same person, though.

Toluidine

I have edited the fairly new p-toluidine article which you wrote. As mentioned on the Talk:p-toluidine page, I am considering moving the p-toluidine article to Toluidine, if possible (so as to keep a record to your contributions), and expanding the article to include all three toluidine isomers. I plan to do this when I have had a chance to prepare an expanded table for all three toluidines. See Talk:p-toluidine. If you have any remarks, let me know. H Padleckas 06:05, 18 July 2005 (UTC)[reply]

Acid-Base Naming

I just pulled the name for the [[Acid-base catalysis article off of the Wikipedia:WikiProject_Missing_encyclopedic_articles, but the Acid catalysis article is certainly more comprehensive. On the name though, which do you think would work better? The other name, and Base catalysis can just be turned into re-dericts, unless mention wants to be made of acid or base specific reactions. Any idea? --Icelight 23:25, July 21, 2005 (UTC)

Fraction (disambiguation)

Fractionation links to Fraction, but unfortunately there's no chemical (etc) fraction listed there. Could you add a link, even a redlink, for an article into Fraction (disambiguation)? Josh Parris ✉ 05:49, 27 July 2005 (UTC)[reply]

I've taken advantage of your creativity. Josh Parris ✉ 06:33, 28 July 2005 (UTC)[reply]

Thanks for the help on the macrocycles article

Thanks for the help with the links on the macrocycle article. I hope that you don't mind, but I updated the knotane article and moved it under a new title, molecular knots. On a quick review of the literature, it seems that the latter term is far more common, while knotane is quite limited in use. Cheers Jeffrey 19:00, 29 July 2005 (UTC)[reply]

Adding articles to Chemistry

This is in response to your comment on my talk page.

I have no problem with people recategorizing articles I've marked under "[[Category:Chemistry]]"; I felt that some of them needed categorization which they were lacking. If they can find subclasses which more appropriately fit, that's fine. The main thing is articles should have categorization on anything relevant and on any category they are related to. This makes it easier for someone to find a relevant article on a subject. If the article lacks an important class, it should be added; the class can be refined later, e.g. organic chemistry or polymer chemistry or pharmaceuticals or whatever, as a change from or in addition to classification under chemistry alone. But getting an initial classification or expanded additional classification(s) in the first place is what's important.

Paul Robinson 02:43, 7 August 2005 (UTC) (User Rfc1394)[reply]

Image:Acetalisation2.gif

Image deletion warning Image:Acetalisation2.gif has been listed at Wikipedia:Images and media for deletion. If you feel that this image should not be deleted, please go there to voice your opinion.

Image:Acetalisation2.gif

Please attach Image:Acetalisation2.gif to an article. By policy (See Wikipedia:What Wikipedia is not), Wikipedia is not an image repository and images need to be put in "an encyclopedic context." Thanks. Nv8200p 17:50, 13 August 2005 (UTC)[reply]

Chemistry

Hi I saw your article Cyclodecapentaene you created. Quite an article, did you really write that from scratch? I'm assuming you did, but it's so full of information and intersting stuff that I'm worried it's copied from somewhere! Don't take that as an offense, it's just that we need to be careful to avoid copyright violations. This was meant more of as a congratulations than it has come out, I swear! Also you may be interested in Wikipedia:Missing science topics, particularly the chemistry one. Thanks - Taxman Talk 19:28, August 15, 2005 (UTC)

Chemistry categories

Hi. Thanks for your note. I've only been deleting the main category if the article appeared to be in a chemstry subcategory. But I don't know much about the subject. I've just been trying to get the many articles in the main cats moved to appropriate subcats. This kind of work seems to languish. But it appears that the chemistry category has been getting smaller, and I'll be happy to get out of the way if someone with more knowledge is taking care of things. Maurreen (talk) 16:28, 16 August 2005 (UTC)[reply]

Pauling's rules -> Orbital hybridisation

Hi, I deleted that redirect because it didn't seem to correspond very closely with what the scienceworld article covered. If the redirect you created is more correct than what SW has, please recreate the redirect. I may have pulled the trigger too quick on that one, sorry, just want to be accurate and comprehensive. - Taxman Talk 18:40, August 25, 2005 (UTC)

On chemistry mechanisms

I think the thing to remember is that chemistry mechanisms (as opposed to named reactions) are grouped for good reasons. An alkyne trimerization is not a cycloaddition (note difference between cycloaddition and cyclization) because it's not concerted, it doesn't follow the woodward-hoffman orbital rules -- these distinctions are particularly important and serve a purpose. In the case of the ene reaction, a link is provided up to the pericyclic reaction page, where you can find ene reactions under group transfer reactions.

Polymer stub question

Hi, Is their a guideline on the use of stubs and categories? I had added {{Polymer-stub}} to a couple of Category:Polymer chemistry or Category:Organic polymers articles. I see that you have removed the {{Polymer-stub}} part. Can articles be both a stub and category? It should make it easier to flag those people might want to work on. Thanks. ChemGardener 00:23, 1 October 2005 (UTC)[reply]

Schiff Bases

What's up with the claim that a Schiff base must have an aryl group connected to the nitrogen? It's my understanding that any imine derived from a primary amine, aromatic or not, is a Schiff base. For example, in rhodopsin, retinal forms a Schiff base with a lysine sidechain. Josh Cherry 13:00, 1 October 2005 (UTC)[reply]

Thanks

Hi, I just wanted to thank you for getting the olefin metathesis article put together earlier this year, I'm really glad we had it in place when the Nobel news came out. Cheers, Walkerma 14:05, 6 October 2005 (UTC)[reply]

  • I will second that! The Nobel Prize was the top story on French TV news, front page in all the papers... I dropped by to ask you to put tabs on the images you uploaded (those used in olefin metathesis) so that I can safely use them in the French article: I assume that they are {{GFDL-self}}, but I cannot put that tab on myself (it has to be the uploader). Keep up the good work! Physchim62 10:48, 7 October 2005 (UTC)[reply]

Dicyclopentadiene comment question

Hi V8rik, I saw you removed the merge notice on dicyclopentadiene. Will it automatically be removed from cyclopentadiene as well? I didn't understand the linkfarm comment. Does that refer to the links between cyclopentadiene and dicyclopentadiene? Thanks. ChemGardener 19:02, 14 October 2005 (UTC)[reply]

  • Thanks for the response. I didn't take the edit comment as particularly aimed at my edit, just trying to understand it. The citing of references and sources and problems thereof are something I'm just learning about. Regards, ChemGardener 21:06, 14 October 2005 (UTC)[reply]

Nicolaou Taxol total synthesis

Hello V8rik, I just (almost randomly) came across your taxol total synthesis page. It looks like quite a labor of love and a nice peice of work. Congrats. If you would like some help with future total synthesis articles, I'd be willing to lend a hand. Have you thought of adding a retrosynthetic analysis before the first section (Synthesis C ring)? I find that retrosynthetic analysis helps people see the larger picture, synthetic strategy, and the real art in synthesis. ~K 17:43, 20 November 2005 (UTC)[reply]

  • Thanks ~K for your suggestions. The retrosynthetic strategy should be included but for now not on my to-do list. What I have in mind with taxol total synthesis is compiling all current efforts (Danishefsky is next) according to one and the same format I hope that the total synthesis collection will give readers a better idea why all these organic reactions exist in the first place. Your help and input is greatly appreciated, you are already doing a great job with the named reactions. V8rik 18:28, 20 November 2005 (UTC)[reply]
Wow! What a fantastic piece of work! I'd been thinking for a while that we needed to have some total syntheses up, to highlight some of the classic syntheses (I'd been thinking of Woodward's strychnine, or would you suggest a different RBW synthesis?). You've done a great job of starting off this class of article, with a landmark synthesis. (However, I hope you're also going to do the synthesis by Holton, which after all was the first Taxol synthesis!). I'd always thought that one of the long term benefits of having a good range of chemical compound articles is that one could write decent synthesis articles, it's wonderful to see that finally come true! Thanks a lot for many, many hours of work, Walkerma 05:15, 21 November 2005 (UTC)[reply]
    • Thanks again! What I have in mind is comparing taxol synthesis by Holton, Danishefsky & paquette. I am working on these at the moment. There is room for a general page on taxol total synthesis that would include retrosynthesis of various strategies (volunteers?). Can somebody help me out with a dynamic 3D taxol image? You are absolutely right, with all the named reactions, reagents and principles in place describing long synthetic schemes is much easier, wiki must take advantage of that. My suggestions for new total synthesis pages would be anything relevant coming out this year. I did see aflatoxin and a new morphine synthesis but what is the most important total synthesis published in 2005? V8rik 00:07, 22 November 2005 (UTC)[reply]
I'll have to ask my colleague, Tony Molinero, he did his PhD on Taxol. I could probably do a page on approaches to morphine synthesis, by updating pages from my PhD dissertation (which is on methodology work, but morphine was a possible application I looked into). Can you let me know the reference to the new synthesis? In grad school I kept up on the latest total syntheses, but now I teach in an undergrad school it's harder to keep my finger on the pulse, and my main area of research interest is in methodology. If I wanted to identify the top synthesis of recent months, I think I would review "News of the Week" in C&E news. I will be going to the Atlanta meeting of the ACS in March, I will keep my ears open. Or will you be there too? Perhaps we could have a coffee or a beer if you are? Cheers, Walkerma 02:44, 22 November 2005 (UTC)[reply]
The most important natural product synthesis of 2005? Good question. I'll give my two bits. Amos B. Smith, III of the University of Pennsylvannia has a long running Discodermolide program. (Discodermolide is another microtubulin stabilizer, like taxol.) They are making Discodermolide analogs on gram scale now for clinical testing. Very exciting stuff with lots of papers out this year. (Org. Lett. 2005, 7(23), 5229-5232, Org. Lett. 2005, 7(21), 4613-4616 and four other this year alone!) There would definitely be plenty to write about. ~K 03:06, 22 November 2005 (UTC)[reply]

Johnson-Corey-Chaykovsky reaction

Hey V8rik, I made some major changes to the Johnson-Corey-Chaykovsky reaction page you wrote a few days ago. I hope you like them. Could you check the page to make sure it's still correct? ~K 20:02, 27 November 2005 (UTC)[reply]


  • Looks great, thanks, I realise now I had the Johnson pic dead wrong........ I am still looking for a way to improve the quality of my images, tried to import ISIS/draw into Illustrator but nothing worked. V8rik 20:10, 27 November 2005 (UTC)[reply]
I would recommend saving the images as TIFF files, then converting them to PNG files using The GIMP. (Walkerma uses IrfanView.) For some reason, the TIFF images are VERY large (pixelwise), so when they are converted and resized smaller to something useful, they end up looking fantastic. Click on the images, and you'll see they are huge. ~K 20:50, 27 November 2005 (UTC)[reply]

Silyl Ethers

Thanks for the correction. I don't know if I did that, but it was clearly a big goof... Eugene Kwan 04:29, 6 December 2005 (UTC)[reply]

Trigonal bipyramid

Is there really a difference between the chemistry and the geometry term? Anyway, in your edit summary you had already answered my question; one of the incoming links is modular origami and I was attempting to disambiguate between a mixup in terminology I had. --HappyCamper 16:37, 17 December 2005 (UTC)[reply]

I put the cleanup tag there because I wanted to clean up the meaning between "trigonal bipyramidal" and "trigonal bipryamid" - the former is the apparently the adjective form of the latter according to WP:RD/L. However, I guess it's not so important. We'll leave the article as is, and when I come across more information, I'll add to it. --HappyCamper 17:31, 17 December 2005 (UTC)[reply]

Chemist

Hey V8rik, I just chanced upon your beautiful Nicolaou Taxol total synthesis. Your chemistry work is state-of-the-art!

I'm looking for a good free chemical drawing program. I've hand-drawn with OpenOffice.org 10 until discovering ISIS/Draw 2.5, but the latter has a bug that prevents it from exporting under Windows 2000. Do you have any advice what I could use? I usually draw small molecules for medication-related pages. JFW | T@lk 22:14, 17 December 2005 (UTC)[reply]

  • well, thanks! have you tried accessing your application under MS Word? Just open MS Word, and include an object, any chemical drawing program like ISIS/draw should automatically in the list. Then save the word file as a HTML page and collect the gif image from the folder that MS automatically creates. Also try ~K's suggestion, download IrfanView (free and reliable), save the drawing as a tiff file, open de image in irfanview (in my application it saves as a triple $ somehow) en save as a png image (compression level 6 on a sale of 9). Important: create the image twice the intended size and twice the indented bond thinkness and crop the image in Wiki. This way you reduce the pixelation and make to images look smooth. Drawback: difficult to work with very large images. The images I did for Pyramidal alkene were done that way. Still improvising so I will keep looking out for the perfect open source solution V8rik 22:34, 17 December 2005 (UTC)[reply]

Cucurbiturils Revision

Regarding your recent update on cucurbiturils. It is commonly accepted when dealing with macromolecules that traditional naming schemes commonly applied to smaller molecules are abandoned as they become too long and cumbersome. Thus more convenient systems of nomenclature are invented. While inclusion of the systematic name for cucurbituril highlights point I do not think that it provides any useful information for someone interested in this subject. Systematic names are not included for the entries of cyclodextrin or calixarene for instance. This was my logic in replacing it with the nomenclature which is quite commonly used. I still beleive that it is probably is not needed. M_stone 16:20, 28 December 2005

  • Hi, thanks for your comment. Your nomenclature addition is very welcome as are the other additions. thanks!. I was somewhat disappointed in the deletions you made, the systematic name is only meant as comic relief but at the same time it demonstrates the power of nomenclature. The systematic name is included for many organic compounds in Wiki and I think it should stay. Also keep in mind one the Wiki directives that state that Wiki is not a paper encyclopedia and has a much wider scope What_wikipedia_is_not#Wikipedia_is_not_a_paper_encyclopedia. You also deleted material but did not delete the associated reference and this confuses the reference system. I do not understand some of your other deletions like the origin of the word (Cucurbitaceae) and the general comment on internal volume. This does not benefit Wiki. Mentioning a commercial supplier in my view does not benefit a reader but providing a link to a supplier datasheet would. V8rik 22:38, 28 December 2005 (UTC)[reply]

I understand your objection to mentioning a commercial supplier. I reverted the naming of cucurbiturils to the origanal statement. I eliminated the CB10 because it seemed odd to mention without mentioning the cavity volumes of the other sizes. I have updated it to include the other sizes as well. I think that the topic is complicated by older references to cucurbituril as only CB[6], while more recently it refers to all sizes. M_stone 18:00, 28 December 2005

Modesty

Hi V8rik. Just thought I'd drop you a note to let you know that you're being too modest with your edits. Most editors agree that major article remodelling proposals (merges and so forth) should count as major edits. Generally, any edit that another editor might want to review or comment upon should not be marked as minor. Keep up the good work, TenOfAllTrades(talk) 18:34, 29 December 2005 (UTC)[reply]

Image Tagging Image:Wittigrearrangement.gif

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  • thanks for the notice I added a GFDL tag so the problem should be solved (created the image myself). When the article was created the copyright issue was still a bit confusing V8rik 23:10, 5 January 2006 (UTC)[reply]

Chemistry portal

Hi, I was wanting to used your picture of taxol for the highlighted picture on the chemistry portal (currently an enzyme pic). I was going to include the following text: "Paclitaxel is an important drug used for the treatment of cancer. Its complex structure provided a challenging target for its total synthesis by the Nicolaou group." Is this OK? Would you be willing make the drawing a little bigger (currently it's a bit small to use)? Cheers, Walkerma 07:40, 6 January 2006 (UTC)[reply]

Thanks, I have now uploaded it. Sorry it took a few days, my internet connection has been very iffy. If you want to make a colour version (in effect showing the retrosynthesis), similar to the picture I linked to above, I will upload that instead. I hope as well that it encourages folks to look at your page on the Nicolaou synthesis. Thank you, Walkerma 20:36, 9 January 2006 (UTC)[reply]

I included the color version as well. same location V8rik 21:01, 9 January 2006 (UTC)[reply]

Thanks, I'll post that. I am adding a comment about the colors relating to the synthetic approach, please tell me if that is wrong. Walkerma 18:07, 10 January 2006 (UTC)[reply]

Neighbouring group participation

Hi, I think that we have the start of a good article. Do you have any ideas of more material which we should add to the page ?Cadmium 22:13, 15 January 2006 (UTC)[reply]

  • The article looks great and a welcome addition to organic chemistry. In terms of content to add I would like to suggest a stereochemistry example. In general I welcome references to original publications with links to abstracts for example those of Winstein V8rik 22:37, 15 January 2006 (UTC)[reply]

Hi, I think that on the NGP page that a distinction should be made between a tosyl group and a tosylate group as they are quite different in nature. For instance TsNH2 is very different to TsONH2. What do you think ? Cadmium 13:26, 17 January 2006 (UTC)[reply]

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Titanium dioxide

I couldn't figure out why you didn't like the merge templates on titanium dioxide and titanium dioxide (B): their use seems perfectly legitimate to me. Physchim62 (talk) 17:02, 25 January 2006 (UTC)[reply]

  • Hi Physchim62. I removed the merge notice for a number of reasons:
  1. the merge notice was not motivated and the direction not specified (it should be a content move to titanium dioxide from titanium dioxide (B)) To me that is inappropriate use of the merge utility
  2. titanium dioxide (B) is a technical topic with relevance to geology and nanotechnology and not of interest for a general article on titanium dioxide.
  3. three other forms of titanium have their own pages.
  4. from the record of user placing the notice I do not see any actual content additions
  5. I have some general reservations regarding merges see User:V8rik#On_mergers

V8rik 17:35, 25 January 2006 (UTC)[reply]

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{{biochem-stub}}

This template added GNRHR to the category Biochemistry stubs, that is a subcategory of "Biochemistry". So, yeah i had provided a category. Besides sending it straight to "Biochemistry" isn't the best way to categorize it. It should go to category 7TM_receptors <= (which is a subcategory of) Transmembrane_receptors <= Receptors <= Proteins <= Molecular biology <= Biochemistry, but after it is a stub no more. We just can't dump everything into the main category, what's the point of having a category tree then? So i'm reverting it back. -- Boris 02:49, 2 February 2006 (UTC)[reply]

Image Tagging Image:Kolbeschmitt.gif

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Image Tagging Image:Reaction-pinner2.png

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Image:BOC application.png

Hello V8rik, I was reading the BOC anhydride article that you started and noticed this image: Image:BOC application.png.

I would like to remove this image from the page for two reasons:

  1. The synthetic steps subsequent the BOC-protection have nothing to do with BOC anhydride. IMO, the image only ends up confusing the reader and diluting the article.
  2. The scheme is confusing and contains many errors.
A) It is difficult to tell the difference between isolated and unisolated intermediates.
B) The structures of unisolated intermediates were not studied, and probably should not be drawn. I would argue they should not be drawn, because we what can be drawn is not fact, but hypothesis. In any case, I believe the unisolated intermediates you have drawn are incorrect. (Second row on right is incorrect. Third row on the right probably does not exist.)
C) t-BuLi has only four carbons.
D) The mechanism of BOC deprotection is incorrect. Isobutylene is formed not t-butyl alcohol, and water is not in the mechanism.

If you feel strongly that retaining this image in the article is the best course of action, then I'm fine with that. However, if you do decide to keep the image, please fix it.

Sorry to be a bother. ~K 01:14, 7 February 2006 (UTC)[reply]

Hi, ~K thanks for your input, let my try to address your issues:

  1. A. the page is about BOC anhydride in general and not just about the protecting agent. The example is included because the reaction product is an important food aroma in the maillard reaction.
  2. B: the image is produced as a schematic with the aim to explain how the reaction works. Intermediates 4 and 6 in the new image are isolated and depicted in the Harrison article.
  3. C: thanks for pointing out the wrong structure for t-BuLi
  4. D: Intermediate 6 is isolated according to the article which makes isobutylene improbable. by the way, in the Solid_phase_peptide_synthesis (last image) the reaction product is a protonated isobutylene which should be target for criticism as well. Water is in the mechanism at some point because the TSOH is hydrated.

If you still feel the article lacks quality I will ask the admins to have it deleted. V8rik 21:45, 7 February 2006 (UTC)[reply]

Hey V8rik, Thanks for responding and numbering the image. Let me respond to each of your points:
1) I accept that. (Sometimes I'm easy to please.)
2a) Without reading the article you would never know which intermediates were isolated and which are hypothesized. I strongly suggest you do not draw hypothetical intermediates because you do not know the structure. If you feel the intermediates are necessary for discussion then enclose them with brackets: [].
2b) The product of the addition of the vinyl lithium to the amide is probably the tetrahedral intermediate, like the Weinreb intermediate. I think it's this because there's a neighboring BOC-group which can stabilize the tetrahedral intermediate in the same way the Weinreb amide stabilizes the tetrahedral intermediate. If the ketone (intermediate 3) was ever liberated it would instantly be attacked by the 2x excess vinyl lithium they use in the reaction. I believe the reason they quench the reaction at -78C is to avoid the collapse of the tetrahedral intermediate before the quench. (Note: The fact that we disagree about the structure of the vinyl lithium addition product tells me that it should not be drawn. The authors of the paper don't even discuss it.)
4a) Everything I know about BOC deprotection tells me that intermediate 6 was not isolated. (BOC group's strong resistance to nucleophiles including moderate stability in refluxing aq. NaOH) So I reread the paper and the supporting info. They do not isolate intermediate 6. They isolate intermediate 7. It is possible to push arrows directly from 5 to 7 without invoking 6 and giving off isobutylene.
4b) The image you refer to in the SPPS article is correct. They neglect to show the t-butyl cation giving off a proton to form isobutylene.
4c) TsOH is difficult to get anhydrous. It's cheap, stable, and easy to handle in its monohydrate form. Just because water is in the pot does not mean it's in the mechanism.
Lastly, I don't feel the image lacks quality. I'm just trying to correct what I feel are errors. Collaborative text is easy; collaborative images are difficult. And anyway, I enjoy debating this stuff because sometimes I learn something new. ~K 05:01, 8 February 2006 (UTC)[reply]


  • Thanks again for your comments, I decided to make an attempt to save the content and skip any mechanism so the image is now a faithful copy of the Harrison article. My remarks;
  1. authors of original papers lack space where wiki does not, so wiki can afford to write down a complete mechanism. Although not hypothesised in the article the current Wiki should present enough guidelines to fill in the blanks. This is not a violation of Not original research but in accordance with do not get technical. The average Wiki reader is not a chemist but should nonetheless be able to understand the content (see Aldol reaction discussion, I do not agree with the consensus reached there)
  2. I have no problem with writing down the lithium compound as the lithium alkoxide but thanks for pointing out that lithium chemistry is far more richer than that
  3. isobutene formation is the logic byproduct when accompanied with carbon dioxide formation but this is a different situation. any thoughts?
Sorry to take so long to get back to you. I think this is a cascading cationic cyclization. After the formation of the tetrahydropyridine, the vinyl ether is protonated. That cation is attacked by the BOC group. Finally, the molecule gives off t-butyl cation, which as you know makes isobutylene. This is just a theory, but plausible. ~K 17:25, 11 February 2006 (UTC)[reply]
  1. thanks, you have me convinced. I will look out for new publications from this group and if they offer more details I can have the article updated. V8rik 18:08, 11 February 2006 (UTC)[reply]
  1. concerning the water: the lithium intermediate is quenched in water after all
  2. I generally try when constructing this type of images to account for all the atoms displayed All too often I see components just disappearing, take for instance the Weinreb article. I also try to keep track of counterions, many sloppy practices there, take for instance the article on choline were 10 editors find it perfectly okay to have a choline displayed without any counterion, (biochemists........). I also try to keep in mind that isolated protons and the likes do not exist and that there should always be a proton donor / acceptor somewhere in the reaction medium.
  3. if the SPPS images displays reactants and products the presence of a t-butyl cation is dead wrong.

Image Tagging Image:Carbene1.gif

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Stille reaction

You deleted a lot of my writing on this article. Could you please put that stuff back? My student wrote the original article as a class assignment, and I had not had a chance to delete the obvious advert that he pasted-in from a manufacturer. I am not sure about if ChemDraw part is his or in violation. But(!) most of the text is my scholarly efforts and should not be removed. Thank you.Smokefoot 20:28, 12 February 2006 (UTC)[reply]

Hi Smokefoot, great idea to have your students contribute to Wiki. Wiki chemistry needs new content! If you want to reconstitute the article please feel free, my concerns though are:

V8rik 21:43, 12 February 2006 (UTC)[reply]

Got it. We'll dump most of it in that case, I sensed a problem and tried to rewrite it last night. We're not complete idiots - only partial ones - and have been pouring in content that I have tried to keep in order - Dess-Martin, SO2Cl2, NiCl2, FSO3H, sulfamic acid, MCPA (when I thought that I was assigning mcpba), Al(OPri)3, AgF2. Really appreciate your help. Smokefoot 21:58, 12 February 2006 (UTC)[reply]
  • V8rik, Upon researching this topic, despite it being a very popular reaction, i had trouble finding resources that intimatly displayed the reaction process, and the few i did locate contradicted other resources. Therefore i used few sources when doing the research. I was not really aware of sci-finder and the other research utilities until lecture last tuesday. In addition, the tables and charts that i used were properly cited (or so i thought). i thought material may be distributed as long as the souce of the resarch was cited, which i thought i did. In response to the acros chart, I thought it would be helpful not only to show an industrial use, but rather a company that uses the specific reagents to carry out the Stille reaction. The table is public access because reagents are pattened and must be displayed for governmental approval. I am sorry if i misunderstood the copyright issues, i assure you that i felt that everthing i put in the artical was properly cited. I will definately take time to revise, and using the new research tools improve and display the page more to the expectiations of the wiki community. I do not mean to damage the integrity of the site, i simply felt i was doing everything appropriately. thanks for the info and i appologize if i did somethng wrong.
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