Journal of Organic Chemistry p. 3994 - 3998 (1980)
Update date:2022-09-26
Topics:
Koenigkramer, Rusty E.
Zimmer, Hans
Diethyl 1-(trimethylsiloxy)-1-phenylmethanephosphonate carbanion 2 is introduced as a novel acyl anion equivalent.When 2 reacts with aldehydes or ketones, a 1,4 oxygen-oxygen silicon migration with subsequent loss of diethyl lithium phosphite is observed.An efficient method utilizing 2 for the preparation of otherwise difficultly obtainable substituted benzoins is presented.Also a novel one-pot method which offers a facile entry into the 2-phenylbenzofuran ring system from 2 via benzoin intermediates using hydriodic acid was developed.
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(1946)