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New Bis(lithiomethyl)silanes: Building Blocks for Organosilanes
Author(s) -
Strohmann Carsten,
Lüdtke Silke,
Wack Eric
Publication year - 1996
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19961290710
Subject(s) - silanes , chemistry , reagent , lithium (medication) , reactivity (psychology) , hydrosilylation , organic chemistry , medicinal chemistry , polymer chemistry , catalysis , silane , medicine , alternative medicine , pathology , endocrinology
The first high yield preparation of non π‐stabilized bis(lithio‐methyl)silanes was performed by the reductive cleavage of C–S bonds with electron transfer reagents. Bis[(phenylthio)‐methyl]silanes synthesized by the reaction of dichlorosilanes with [(phenylthio)methyl]lithium were transformed to the corresponding bis(lithiomethyl)silanes 7 by reaction with lithium naphthalenide (LiC 10 H 8 ) or lithium p,p ′‐di‐ tert ‐butyl‐biphenylide (LiDBB) as an electron transfer reagent and were characterized by their reaction with Bu 3 SnCl. The C–S bonds of bis[(phenylthio)methyl]silanes can be cleaved selectively making possible the introduction of two different groups. – The silicon atom plays a central role in the reactivity of the presented structural types. The bis(lithiomethyl)silanes are used as new building blocks for the preparation of organosilanes, Si–H‐functionalized organosilanes, and 1,3‐disilacyclobutanes containing SiCH 2 Si structural units.