Unusual lithium transfer reactions in lithium-substituted organo-silicon compounds. Reinvestigation of the reaction of 1,8-di-lithionaphthalene with trimethylchlorosilane

R. J. Wroczynski; Mary W. Baum; Daniel Kost; Kurt Mislow; Steven C. Vick; Dietmar Seyferth

doi:10.1016/S0022-328X(00)81092-X

Unusual lithium transfer reactions in lithium-substituted organo-silicon compounds. Reinvestigation of the reaction of 1,8-di-lithionaphthalene with trimethylchlorosilane

R. J. Wroczynski, Mary W. Baum, Daniel Kost, Kurt Mislow, Steven C. Vick, Dietmar Seyferth

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

30 Scopus citations

Abstract

The product of the reaction of 1,8-dilithionaphthalene with trimethylchlorosilane is 2-(1-naphthyl)-2,4,4-trimethyl-2,4-disilapentane rather than 1,8-bis(trimethylsilyl)naphthalene as previously reported. A novel, presumably intramolecular, metalation process transfers the organolithium function in 1-trimethylsilyl-8-lithionaphthalene to a methyl substituent on the trimethylsilyl group, and it is this new organolithium reagent which reacts with the second mole of trimethylchlorosilane. Ring-opening of 1,1-dimethyl-2,3-bis(trimethylsilyl)-1-silirene by methyllithium is followed by a similar transfer of the organolithium function from the vinylic carbon atom to a methyl group on silicon.

Original language	English
Pages (from-to)	C29-C33
Journal	Journal of Organometallic Chemistry
Volume	170
Issue number	2
DOIs	https://doi.org/10.1016/S0022-328X(00)81092-X
State	Published - 1 May 1979
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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title = "Unusual lithium transfer reactions in lithium-substituted organo-silicon compounds. Reinvestigation of the reaction of 1,8-di-lithionaphthalene with trimethylchlorosilane",

abstract = "The product of the reaction of 1,8-dilithionaphthalene with trimethylchlorosilane is 2-(1-naphthyl)-2,4,4-trimethyl-2,4-disilapentane rather than 1,8-bis(trimethylsilyl)naphthalene as previously reported. A novel, presumably intramolecular, metalation process transfers the organolithium function in 1-trimethylsilyl-8-lithionaphthalene to a methyl substituent on the trimethylsilyl group, and it is this new organolithium reagent which reacts with the second mole of trimethylchlorosilane. Ring-opening of 1,1-dimethyl-2,3-bis(trimethylsilyl)-1-silirene by methyllithium is followed by a similar transfer of the organolithium function from the vinylic carbon atom to a methyl group on silicon.",

author = "Wroczynski, {R. J.} and Baum, {Mary W.} and Daniel Kost and Kurt Mislow and Vick, {Steven C.} and Dietmar Seyferth",

note = "Funding Information: Acknowledgment. We thank the National (CHE77-07665) and the Air Force Off$c_e (AF-AFOSR-79-0007) for support of this",

year = "1979",

month = may,

day = "1",

doi = "10.1016/S0022-328X(00)81092-X",

language = "English",

volume = "170",

pages = "C29--C33",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier B.V.",

number = "2",

}

Unusual lithium transfer reactions in lithium-substituted organo-silicon compounds. Reinvestigation of the reaction of 1,8-di-lithionaphthalene with trimethylchlorosilane. / Wroczynski, R. J.; Baum, Mary W.; Kost, Daniel et al.
In: Journal of Organometallic Chemistry, Vol. 170, No. 2, 01.05.1979, p. C29-C33.

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

TY - JOUR

T1 - Unusual lithium transfer reactions in lithium-substituted organo-silicon compounds. Reinvestigation of the reaction of 1,8-di-lithionaphthalene with trimethylchlorosilane

AU - Wroczynski, R. J.

AU - Baum, Mary W.

AU - Kost, Daniel

AU - Mislow, Kurt

AU - Vick, Steven C.

AU - Seyferth, Dietmar

N1 - Funding Information: Acknowledgment. We thank the National (CHE77-07665) and the Air Force Off$c_e (AF-AFOSR-79-0007) for support of this

PY - 1979/5/1

Y1 - 1979/5/1

N2 - The product of the reaction of 1,8-dilithionaphthalene with trimethylchlorosilane is 2-(1-naphthyl)-2,4,4-trimethyl-2,4-disilapentane rather than 1,8-bis(trimethylsilyl)naphthalene as previously reported. A novel, presumably intramolecular, metalation process transfers the organolithium function in 1-trimethylsilyl-8-lithionaphthalene to a methyl substituent on the trimethylsilyl group, and it is this new organolithium reagent which reacts with the second mole of trimethylchlorosilane. Ring-opening of 1,1-dimethyl-2,3-bis(trimethylsilyl)-1-silirene by methyllithium is followed by a similar transfer of the organolithium function from the vinylic carbon atom to a methyl group on silicon.

AB - The product of the reaction of 1,8-dilithionaphthalene with trimethylchlorosilane is 2-(1-naphthyl)-2,4,4-trimethyl-2,4-disilapentane rather than 1,8-bis(trimethylsilyl)naphthalene as previously reported. A novel, presumably intramolecular, metalation process transfers the organolithium function in 1-trimethylsilyl-8-lithionaphthalene to a methyl substituent on the trimethylsilyl group, and it is this new organolithium reagent which reacts with the second mole of trimethylchlorosilane. Ring-opening of 1,1-dimethyl-2,3-bis(trimethylsilyl)-1-silirene by methyllithium is followed by a similar transfer of the organolithium function from the vinylic carbon atom to a methyl group on silicon.

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DO - 10.1016/S0022-328X(00)81092-X

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Unusual lithium transfer reactions in lithium-substituted organo-silicon compounds. Reinvestigation of the reaction of 1,8-di-lithionaphthalene with trimethylchlorosilane

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