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The Diels‐Alder Reaction of 2,3‐Disulfur‐Substituted 1,3‐Butadienes
Author(s) -
Chou ShangShing P.,
Sun DerJen
Publication year - 1988
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.198800066
Subject(s) - chemistry , regioselectivity , substituent , diene , diels–alder reaction , reactivity (psychology) , sulfonyl , lewis acids and bases , medicinal chemistry , polar effect , organic chemistry , polymer chemistry , alkyl , catalysis , medicine , natural rubber , alternative medicine , pathology
The 2,3‐disulfur‐substituted 1,3‐dienes (1) can be readily prepared from their stable 3‐sulfolene precursors (2) by thermal extrusion of SO 2 . The Diels‐Alder reaction of diene (1) with several dienophiles has been studied. The substituent effect on the reactivity and regioselectivity follows the order of PhS >PhSO >PhSO 2 . Lewis acid can greatly increase the regioselectivity of this reaction. The diene (1c), bearing a strong electron‐withdrawing sulfonyl group, also reacted as a dienophile.