Thial

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Chemical structure of a thial.

A thial or thioaldehyde is a functional group in organic chemistry which is similar to an aldehyde, RC(O)H, in which a sulfur (S) atom replaces the oxygen (O) atom of the aldehyde (R represents an alkyl or aryl group). Thioaldehydes are even more reactive than thioketones. Unhindered thioaldehydes are generally too reactive to be isolated — for example, thioformaldehyde, H2C=S, condenses to the cyclic trimer 1,3,5-trithiane while thioacrolein, H2C=CHCH=S, formed by decomposition of allicin from garlic, undergoes a self Diels-Alder reaction giving isomeric vinyldithiins.[1][2] While thioformaldehyde is highly reactive, it is thermodynamically quite stable and is found in interstellar space along with its mono- and di-deuterated isotopologues.[3] With sufficient steric bulk, however, stable thioaldehydes can be isolated.[4]

In early work, the existence of thioaldehydes was inferred by trapping processes. For instance the reaction of Fc2P2S4 with benzaldehyde was proposed to form thiobenzaldehyde, which forms a cycloadduct with the dithiophosphine ylides to form a C2PS3 ring.[5]

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References[edit]

  1. ^ H. W. Kroto, B. M. Landsberg, R. J. Suffolk, A. Vodden (1974). "The photoelectron and microwave spectra of the unstable species thioacetaldehyde, CH3CHS, and thioacetone, (CH3)2CS". Chem. Phys. Lett. 29 (2): 265–269. Bibcode:1974CPL....29..265K. doi:10.1016/0009-2614(74)85029-3. 
  2. ^ E. Block (2010). Garlic and Other Alliums: The Lore and the Science. Royal Society of Chemistry. ISBN 0-85404-190-7. 
  3. ^ http://www.astro.uni-koeln.de/site/vorhersagen/molecules/ism/H2CS.html
  4. ^ N. Takeda, N. Tokitoh, R. Okazaki (1997). "Synthesis, Structure, and Reactions of the First Rotational Isomers of Stable Thiobenzaldehydes, 2,4,6-Tris[bis(trimethylsilyl)methyl]thiobenzaldehydes". Chem. Eur. J. 3: 62–69. doi:10.1002/chem.19970030111. 
  5. ^ A. Capperucci, A. Degl’Innocenti, P. Scafato, P. Spagnolo (1995). "Synthetic Applications of Bis(trimethylsilyl)sulfide: Part II. Synthesis of Aromatic and Heteroaromatic o-Azido-Thioaldehydes". Chemistry Letters 24 (2): 147. doi:10.1246/cl.1995.147.