Journal of Oleo Science
Online ISSN : 1347-3352
Print ISSN : 1345-8957
ISSN-L : 1345-8957
Symposium on the Chemistry of Terpenes, Essential Oils and Aromatics (TEAC)
Tandem Brook Rearrangement/Silicon Polonovski Reaction via Oxidative Generation of Ammonium Ylides
Hiromasa ShibuyaTakahiro NakagoSeiichi InoueYujiro HoshinoKiyoshi Honda
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2017 Volume 66 Issue 8 Pages 833-842

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Abstract

A tandem Brook rearrangement/silicon Polonovski reaction has been achieved by in situ generation of ammonium ylides via the oxidation of α-silyl-tertiary amines. Furthermore, we found that the oxidation of N-(1-cyano-1-silyl)methyl-tertiary amines with peracids induced the tandem Brook rearrangement/silicon Polonovski reaction/fragmentation to give formamide derivatives in moderate yields.

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© 2017 by Japan Oil Chemists' Society
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