PREPARATION AND SYNTHETIC UTILITY OF 2-METHYLSELENOMETHYL ALLYL METHYL SELENIDE - A VALUABLE PRECURSOR TO 2-SILYLMETHYLALLYLLITHIUMS

Citation
A. Krief et al., PREPARATION AND SYNTHETIC UTILITY OF 2-METHYLSELENOMETHYL ALLYL METHYL SELENIDE - A VALUABLE PRECURSOR TO 2-SILYLMETHYLALLYLLITHIUMS, Synlett, (11), 1998, pp. 1219
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
09365214
Issue
11
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):11<1219:PASUO2>2.0.ZU;2-2
Abstract
3-Lithio-2-[silylmethyl]propenes, easily prepared from 3-methylseleno- 2-[silylmethyl]propenes by the cleavage of the C-Se bond, are useful i ntermediates for the preparation of a variety of functionalised allyls ilanes. These allylsilanes are interesting building blocks, used for e xample, as annelating agents in the efficient synthesis of spiroketals by the Intramolecular Silyl-Modified Sakurai (ISMS) cyclisation. The methodology described in this article provides also an expedient route to a range of heterosubstituted methylselenopropenes, which are valua ble precursors to a range of useful heterosubstituted allyllithium rea gents. Finally, a one-step preparation of functionalised allylsilanes from readily available 3-methylseleno-2-[methylselenomethyl]propene is reported.