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Endo–exo isomerism

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This is an old revision of this page, as edited by Chemkostya (talk | contribs) at 11:23, 8 October 2021 (the image was wrong according to the same references to IUPAC in the article. x ≥ y > z > 0, while z=0 in the suggested example). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

endo–exo isomerism is a special type of stereoisomerism found in organic compounds with a substituent on a bridged ring system. The prefix endo is reserved for the isomer with the substituent located closest, or "syn", to the longest bridge. The prefix exo is reserved for the isomer with the substituent located farthest, or "anti", to the longest bridge. Here "longest" and "shortest" refer to the number of atoms that comprise the bridge. This type of molecular geometry is found in norbornane systems such as dicyclopentadiene.

The terms endo and exo are used in a similar sense in discussions of the stereoselectivity in Diels–Alder reactions.

References

  • IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "endo, exo, syn, anti". doi:10.1351/goldbook.E02094
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