PDF herunterladen
Synthesis 1992; 1992(1/2): 69-74
DOI: 10.1055/s-1992-34186
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

The Regiochemistry of the Protodesilylation of Some Cyclopropylmethylsilanes Derived from Allylsilanes

Ian Fleming* , Philip E. J. Sanderson, Nicholas K. Terrett
  • *University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, England
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
18. September 2002 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

Simmons-Smith type methylenation of allylsilanes, followed by protodesilylation, can be used to achieve overall the SE2′ replacement of the silyl group by a methyl group. The regioselectivity is good for protonation on the methylene carbon of the cyclopropylmethylsilanes 11, 17, 20 and 23, but the low stereoselectivity in the formation of the cyclopropylmethylsilane 26 and its failure to undergo clean protodesilylation make the method of limited use.