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Metal-catalyzed ylide formation and [2,3] sigmatropic rearrangement of allyl sulfides with trimethylsilyldiazomethane

✍ Scribed by David S. Carter; David L. Van Vranken

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 230 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00112-4

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✦ Synopsis

Trimethylsilyldiazomethane is compared with ethyl diazoacetate for the rhodium, copper, and cobalt catalyzed formation and [2,3] rearrangement of allylsulfonium ylides. At room temperature, the reaction can be carried out using the allyl sulfide as the limiting reagent by slow addition of 3 equivalents of the diazo compound. Slightly better yields were obtained with trimethylsilyldiazomethane than with ethyl diazoacetate.

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