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Reactions of allylsilanes with quinones. Synthesis of allyl-substituted hydroquinones

โœ Scribed by Akira Hosomi; Hideki Sakurai

Book ID
104235718
Publisher
Elsevier Science
Year
1977
Tongue
French
Weight
206 KB
Volume
18
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Allyl-substituted hydroquinones have been prepared conveniently by the reaction of allylsilanes with various p-quinones in the presence of a Lewis acid in moderate yield. p-Allylquinols were also obtained regioselectively from 2, 6disubstituted quinones.

Allylation of quinones 2-5 is an important reaction for preparing isoprenoid quinones6-' which play an important role in biological processes 10-12 such as electron transport, blood clotting, and oxidative phosphorylation. We wish to report herein a novel and convenient allylation of quinones with allylsilanes.

Thus, in the course of studies on the further application of allylsilanes to organic synthesis, 13 it has been found that the reaction of allylsilanes with various quinones activated by a Lewis acid in dichloromethane produces the corresponding allyl-substituted hydroquinones and/or p-allylquinols in moderate yield.

Although the type of the product depends upon the substrate employed,

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