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Dialkylative Cyclization Reactions of 3‐(Phenylthio)‐3‐Sulfolenes
Author(s) -
Chou ShangShiag P.,
Sung ChinChung,
Sun DerJen
Publication year - 1992
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.199200057
Subject(s) - bicyclic molecule , chemistry , methylene , medicinal chemistry , stereochemistry
3‐(Phenylthio)‐3‐sulfolene (4) underwent bridged dialkylative cyclization with 2‐methylene‐1,3‐diiodopropane to give the bridged bicyclic 3‐sulfolene 23, and spirodialkylation with 1,4‐diiodobutane and 1,5‐diiodopentane to give the spiro bicyclic 3‐sulfolenes 15 as the major product. The reaction of 4 with 1,3‐diiodopropane led to the fused bicyclic 2‐sulfolene 12. 3‐(Phenylthio)‐3‐sulfolenes bearing an ω‐iodoalkyl group at the C‐2 position gave the fused bicyclic 2‐sulfolenes 28 and/or the spiro bicyclic 3‐sulfolene 29 depending on the chain length.