| Identification | Back Directory | [Name]
Silane, 1,1'-[(1E,3E)-1,3-butadiene-1,4-diyl]bis[1,1,1-trimethyl- | [CAS]
22430-47-3 | [Synonyms]
Silane, 1,1'-[(1E,3E)-1,3-butadiene-1,4-diyl]bis[1,1,1-trimethyl- | [Molecular Formula]
C10H22Si2 | [MOL File]
22430-47-3.mol | [Molecular Weight]
198.453 |
| Hazard Information | Back Directory | [Physical properties]
bp 46–49°C/15 mmHg; n20
D 1.4679. | [Uses]
(1E,3E)-1,4-Bis(trimethylsilyl)-1,3-
butadiene is a building block for the stereodefined construction of conjugated
polyenyl chains.
Bromine addition leads to a tetrabromo
derivative which can be bromodesilylated to (1Z,3Z)-1,4-
dibromobutadiene (eq 3). | [Preparation]
coupling of the Grignard reagent derived
from (E)-2-(trimethylsilyl)-1-bromoethylene with the same
bromo derivative leads to the silyldiene in 51% yield;a
higher yield (62%) is obtained by reaction of bis(trimethylsilyl)-
methyllithium with (E)-3-(trimethylsilyl)-2-propenal.Other
procedures involve the Pd0-catalyzed demercuration of bis[(E)-
(2-trimethylsilylvinyl)]mercury, prepared from (E)-2-(trimethylsilyl)-
1-lithioethylene and HgCl2 (77% yield),or the
reaction of (E)-1,4-bis(trimethylsilyl)-2-butene with n-BuLi
and TMEDA and subsequent oxidation with HgCl2 of the
isolated bis-lithiated species, stabilized by complexation with
TMEDA (57% yield). |
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