✦ LIBER ✦

A simple synthesis of allylsilanes via tris[(trimethylsilyl)methyl]borane

✍ Scribed by Kung K Wang; Sujitra Dhumrongvaraporn

Book ID: 104227469
Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 209 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)95897-0

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✦ Synopsis

Allylsilanes were prepared by protonation or alkylation of lithium 1-alkynyltris[(trimethylsilyl)methyl]borates followed by protonolysis or treatment with aqueous sodium hydroxide and iodine.

We have shown in the preceding note one example of using tris[(trimethylsilyl)methyllborane for the preparation of an allylsilane.l We now report an extension of this work to the synthesis of a variety of allylsilanes using the same organoborate reaction but with the migration of the (trimethylsilyl)methyl group induced by other electrophiles.

2 The migration of the second (trimethylsilyl)methyl group was also promoted by treating the resulting alkenylborane with aqueous sodium hydroxide followed by iodine as described previously. 3 A summary of the results is given in Table . 4 ( Me3SiCH2)3B LiC EC--R * EX (Me,SiCH,),B w VR Me,Si fiE

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