Bulletin of the Chemical Society of Japan p. 1057 - 1062 (1999)
Update date:2022-08-12
Topics:
Tanikaga, Rikuhei
Nishikawa, Takeshi
Tomita, Naoki
Diastereoisomeric 4-(t-butyl)-1-(phenylsulfonyl)cyclohexanes 3 and 4- (t-butyl)-2-phenylsulfonyl-1-cyclohexanols 10 were subjected to H-D exchange, methylation, and allylation. The anions generated from 3 and 10 rapidly isomerized to those having a sulfonyl group in an equatorial position to form both equatorial and axial carbanions, in which a slight difference was found toward the subsequent electrophilic attack. The reaction of the dianion of 10 was little affected by an adjacent oxyanion and its countercation. The steric requirement of a bulky aggregate containing a sulfonyl group and a THF- solvated metal counterion may play an important role in the stereochemical behavior of α-sulfonyl carbanions.
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