Synthesis and striking reactivity of an isolable tetrasilyl-substituted trisilaallene

Hiroaki Tanaka; Shigeyoshi Inoue; Masaaki Ichinohe; Matthias Driess; Akira Sekiguchi

doi:10.1021/om200405e

Synthesis and striking reactivity of an isolable tetrasilyl-substituted trisilaallene

Hiroaki Tanaka, Shigeyoshi Inoue, Masaaki Ichinohe, Matthias Driess, Akira Sekiguchi

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Abstract

The first silyl-substituted Si₃-allene, namely 1,1,3,3-tetrakis(di-tert-butylmethylsilyl)trisilaallene (4), was prepared as an air- and moisture-sensitive red solid by the reaction of the dilithiosilane (^tBu₂MeSi)₂SiLi₂ with the dichlorosilylene-NHC complex:SiCl₂?NHC (NHC = 1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidene) in benzene at room temperature. Remarkably, the reaction of 4 with methanol proceeds regioselectively to form only the 3,3-dimethoxypentasilane derivative 5, in contrast to the case for a previously reported trisilaallene. In addition, 4 undergoes unprecedented thermal isomerization to tetrakis(di-tert-butylmethylsilyl)cyclotrisilene (7).

Original language	English
Pages (from-to)	3475-3478
Number of pages	4
Journal	Organometallics
Volume	30
Issue number	13
DOIs	https://doi.org/10.1021/om200405e
State	Published - 11 Jul 2011
Externally published	Yes

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title = "Synthesis and striking reactivity of an isolable tetrasilyl-substituted trisilaallene",

abstract = "The first silyl-substituted Si3-allene, namely 1,1,3,3-tetrakis(di-tert-butylmethylsilyl)trisilaallene (4), was prepared as an air- and moisture-sensitive red solid by the reaction of the dilithiosilane (tBu2MeSi)2SiLi2 with the dichlorosilylene-NHC complex:SiCl2?NHC (NHC = 1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidene) in benzene at room temperature. Remarkably, the reaction of 4 with methanol proceeds regioselectively to form only the 3,3-dimethoxypentasilane derivative 5, in contrast to the case for a previously reported trisilaallene. In addition, 4 undergoes unprecedented thermal isomerization to tetrakis(di-tert-butylmethylsilyl)cyclotrisilene (7).",

author = "Hiroaki Tanaka and Shigeyoshi Inoue and Masaaki Ichinohe and Matthias Driess and Akira Sekiguchi",

year = "2011",

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TY - JOUR

T1 - Synthesis and striking reactivity of an isolable tetrasilyl-substituted trisilaallene

AU - Tanaka, Hiroaki

AU - Inoue, Shigeyoshi

AU - Ichinohe, Masaaki

AU - Driess, Matthias

AU - Sekiguchi, Akira

PY - 2011/7/11

Y1 - 2011/7/11

N2 - The first silyl-substituted Si3-allene, namely 1,1,3,3-tetrakis(di-tert-butylmethylsilyl)trisilaallene (4), was prepared as an air- and moisture-sensitive red solid by the reaction of the dilithiosilane (tBu2MeSi)2SiLi2 with the dichlorosilylene-NHC complex:SiCl2?NHC (NHC = 1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidene) in benzene at room temperature. Remarkably, the reaction of 4 with methanol proceeds regioselectively to form only the 3,3-dimethoxypentasilane derivative 5, in contrast to the case for a previously reported trisilaallene. In addition, 4 undergoes unprecedented thermal isomerization to tetrakis(di-tert-butylmethylsilyl)cyclotrisilene (7).

AB - The first silyl-substituted Si3-allene, namely 1,1,3,3-tetrakis(di-tert-butylmethylsilyl)trisilaallene (4), was prepared as an air- and moisture-sensitive red solid by the reaction of the dilithiosilane (tBu2MeSi)2SiLi2 with the dichlorosilylene-NHC complex:SiCl2?NHC (NHC = 1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidene) in benzene at room temperature. Remarkably, the reaction of 4 with methanol proceeds regioselectively to form only the 3,3-dimethoxypentasilane derivative 5, in contrast to the case for a previously reported trisilaallene. In addition, 4 undergoes unprecedented thermal isomerization to tetrakis(di-tert-butylmethylsilyl)cyclotrisilene (7).

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U2 - 10.1021/om200405e

DO - 10.1021/om200405e

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JO - Organometallics

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IS - 13

ER -

Synthesis and striking reactivity of an isolable tetrasilyl-substituted trisilaallene

Abstract

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