Bulletin of the Chemical Society of Japan p. 3593 - 3599 (1991)
Update date:2022-08-05
Topics: Synthesis Ketone Sterically hindered Structure Chemical properties
Nakayama, Juzo
Hirashima, Atsushi
Yokomori, Yoshinobu
A sterically hindered ketone 2,2,5,5-tetramethyl-4,4-diphenyl-3-thiolanone (1), was synthesized in two steps starting from 2,2,4,4-tetramethyl-1,5-diphenyl-1,5-dione.The carbonyl group of 1 is unreactive toward a series of nucleophiles which are bulkier than hydride or its equivalents.The observed unreactivity is ascribed to the steric hindrance enhanced by the two methyl groups on C-5 ("buttressing" effect).The results of an X-ray single crystal structure analysis of 1 is also described.
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