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Intramolecular Diels‐Alder Reactions via 3‐(Phenylthio)‐4‐(Trimethylsilyl)‐3‐Sulfolene
Author(s) -
Chou ShangShing P.,
Lee ChienMing
Publication year - 1991
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.199100082
Subject(s) - chemistry , intramolecular force , bicyclic molecule , toluene , deprotonation , yield (engineering) , diels–alder reaction , medicinal chemistry , trimethylsilyl , organic chemistry , stereochemistry , catalysis , ion , materials science , metallurgy
Deprotonation of the title compound 2 followed by treatment with 5‐iodo‐1‐pentene or 6‐iodo‐l‐hexene gave the alkylated products 3 and 4 which upon refluxing in toluene yielded the dienes 8a and 8b. Intramolecular Diels‐Alder reactions were achieved by heating the dienes 8a and 8b in toluene in a sealed tube at 160–180°C to give bicyclo[4.3.0]nonene 9 and bicyclo[4.4.0]decene 10, respectively, in good yield. The stereochemistry of the cyclization products was determined, and was rationalized by comparison of the possible transition states involved.