Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Electron Transfer vs. Nucleophilic Addition of Ketene Silyl Acetals with Halogenated p-Benzoquinone Derivatives
Shunichi FukuzumiMorifumi FujitaGen-etsu MatsubayashiJunzo Otera
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1993 Volume 22 Issue 8 Pages 1451-1454

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Abstract

A β,β-dimethyl-substituted ketene silyl acetal reduces p-chloranil to produce the carbon-oxygen adduct, the hydrolysis of which yields the corresponding hydro-quinone ether (3). The structure of 3 has been determined by the X-ray crystal analysis. On the other hand, the reaction of a nonsubstituted ketene silyl acetal with p-fluoranil yields the carbon-carbon adduct selectively. The mechanistic difference between the C-O and C-C bond formation is elucidated based on the kinetic study.

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© 1993 The Chemical Society of Japan
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