The Regiochemistry of the Protodesilylation of Some Cyclopropylmethylsilanes Derived from Allylsilanes

Ian Fleming; Philip E. J. Sanderson; Nicholas K. Terrett

doi:10.1055/s-1992-34186

Synthesis 1992; 1992(1/2): 69-74
DOI: 10.1055/s-1992-34186

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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

Abstract

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Simmons-Smith type methylenation of allylsilanes, followed by protodesilylation, can be used to achieve overall the S_E2′ 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.

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