Bis[bis(methylthio)lithiomethyl]dimethylsilanes: A useful reagent for the synthesis of polysilacarbacycles via disilylation

Masaki Shimizu; Masayuki Iwakubo; Yasushi Nishihara; Tamejiro Hiyama

doi:10.1016/S0040-4039(98)00457-2

Bis[bis(methylthio)lithiomethyl]dimethylsilanes: A useful reagent for the synthesis of polysilacarbacycles via disilylation

Masaki Shimizu, Masayuki Iwakubo, Yasushi Nishihara, Tamejiro Hiyama

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

Bis[bis(methylthio)lithiomethyl]dimethylsilane was generated from bis[bis(methylthio)methyl]dimethylsilane by deprotonation with t-BuLi in THF and allowed to react with various dichloro(poly)silanes to give the corresponding 4- to 7-membered polysilacarbacycles in moderate to good yields. The methylthio groups in the cyclized products were readily removed by radical reduction with Bu₃SnH.

Original language	English
Pages (from-to)	3193-3196
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	20
DOIs	https://doi.org/10.1016/S0040-4039(98)00457-2
Publication status	Published - May 14 1998
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{252d3473b33e40daa706e00e2a0f5735,

title = "Bis[bis(methylthio)lithiomethyl]dimethylsilanes: A useful reagent for the synthesis of polysilacarbacycles via disilylation",

abstract = "Bis[bis(methylthio)lithiomethyl]dimethylsilane was generated from bis[bis(methylthio)methyl]dimethylsilane by deprotonation with t-BuLi in THF and allowed to react with various dichloro(poly)silanes to give the corresponding 4- to 7-membered polysilacarbacycles in moderate to good yields. The methylthio groups in the cyclized products were readily removed by radical reduction with Bu3SnH.",

author = "Masaki Shimizu and Masayuki Iwakubo and Yasushi Nishihara and Tamejiro Hiyama",

note = "Funding Information: Acknowledgment: The present work was partially supported by a Grant-in-Aid (No. 07405042) for Scientific Research from The Ministry of Education, Science, Sports and Culture and a Grant-in-Aid for {"}Research for the Future{"} Program (96Rl1601) from The Japan Society of the Promotion of Science. We thank Shin-Etsu Chemical Co. Ltd. for the generous gifts of organosilicon compounds.",

year = "1998",

month = may,

day = "14",

doi = "10.1016/S0040-4039(98)00457-2",

language = "English",

volume = "39",

pages = "3193--3196",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "20",

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TY - JOUR

T1 - Bis[bis(methylthio)lithiomethyl]dimethylsilanes

T2 - A useful reagent for the synthesis of polysilacarbacycles via disilylation

AU - Shimizu, Masaki

AU - Iwakubo, Masayuki

AU - Nishihara, Yasushi

AU - Hiyama, Tamejiro

N1 - Funding Information: Acknowledgment: The present work was partially supported by a Grant-in-Aid (No. 07405042) for Scientific Research from The Ministry of Education, Science, Sports and Culture and a Grant-in-Aid for "Research for the Future" Program (96Rl1601) from The Japan Society of the Promotion of Science. We thank Shin-Etsu Chemical Co. Ltd. for the generous gifts of organosilicon compounds.

PY - 1998/5/14

Y1 - 1998/5/14

N2 - Bis[bis(methylthio)lithiomethyl]dimethylsilane was generated from bis[bis(methylthio)methyl]dimethylsilane by deprotonation with t-BuLi in THF and allowed to react with various dichloro(poly)silanes to give the corresponding 4- to 7-membered polysilacarbacycles in moderate to good yields. The methylthio groups in the cyclized products were readily removed by radical reduction with Bu3SnH.

AB - Bis[bis(methylthio)lithiomethyl]dimethylsilane was generated from bis[bis(methylthio)methyl]dimethylsilane by deprotonation with t-BuLi in THF and allowed to react with various dichloro(poly)silanes to give the corresponding 4- to 7-membered polysilacarbacycles in moderate to good yields. The methylthio groups in the cyclized products were readily removed by radical reduction with Bu3SnH.

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U2 - 10.1016/S0040-4039(98)00457-2

DO - 10.1016/S0040-4039(98)00457-2

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JO - Tetrahedron Letters

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IS - 20

ER -

Bis[bis(methylthio)lithiomethyl]dimethylsilanes: A useful reagent for the synthesis of polysilacarbacycles via disilylation

Abstract

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