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2‐Chloro‐1,4‐benzodithiin 1,1,4,4‐Tetraoxide – A Conjunctive Dienophile for the Preparation of Tetrasubstituted Polycyclic Olefins
Author(s) -
De Lucchi Ottorino,
Cossu Sergio
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199812)1998:12<2775::aid-ejoc2775>3.0.co;2-t
Subject(s) - chemistry , cycloaddition , adduct , diene , molecule , medicinal chemistry , diels–alder reaction , organic chemistry , catalysis , natural rubber
Abstract 2‐Chloro‐1,4‐benzodithiin 1,1,4,4‐tetraoxide 11 is a reactive dienophile that forms Diels‐Alder adducts with a number of dienes. Adducts 17a–j undergo facile dehydrochlorination to give 2,3‐substituted 1,4‐benzodithiin tetraoxides 18a–j , which react further with another molecule of diene (the same or a different one) affording the “double” adducts 19‐23 . Upon reductive desulfonylation with sodium amalgam, the latter are transformed to tetrasubstituted polycyclic olefins 24‐27 . These olefins correspond to the cycloadducts that would theoretically have been formed by the cycloaddition of diatomic carbon with two molecules of diene, reacting in a Diels‐Alder fashion.