ChemInform Abstract: The Sila-Wittig Rearrangement.

✍ Scribed by A. KAWACHI; N. DOI; K. TAMAO

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 32 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199717168

✦ Synopsis

The Sila-Wittig Rearrangement.

-The first examples of silicon analogues to the (2,3)-Wittig rearrangements which involve intramolecular migration of an allyl group from an oxygen or nitrogen to silicon are described. The rearrangement is enhanced by a crown ether. Thus the reaction of (I) in the presence of 12-crown-4 affords (III) in 55% yield even at -78 . degree.C. However, the method is applicable only to tertiary allyloxy derivatives. But these rearrangements represent a novel route from allyl alcohols or allylamines to sila-functionalized allylsilanes in a regiocontrolled fashion. -(KAWACHI,