Crystalline alkyl-lithiums from α-trimethylsilyl-substituted o-xylenes; x-ray crystal structure of [{o-C6H4(CHSiMe 3)2}{Li(tmeda)}2] (tmeda = Me 2NCH2CH2NMe2)

Michael F. Lappert; Colin L. Raston; Brian W. Skelton; Allan H. White

doi:10.1039/C39820000014

Crystalline alkyl-lithiums from α-trimethylsilyl-substituted o-xylenes; x-ray crystal structure of [{o-C₆H₄(CHSiMe ₃)₂}{Li(tmeda)}₂] (tmeda = Me ₂NCH₂CH₂NMe₂)

Michael F. Lappert, Colin L. Raston, Brian W. Skelton, Allan H. White

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

63 Citations (Scopus)

Abstract

Reaction of [o-C₆H₄(CHRR′)(CHR″R‴) ] (R, R′, R″, R‴ = H or SiMe₃) with LiBu ⁿ in n-hexane in the presence of Me₂NCH₂CH ₂NMe₂ (tmeda) or MeN(CH₂CH₂NMe ₂)₂ (pmdeta) results in selective lithiation of the α-carbon in a manner dependent on the nature of the associated substituents and the tertiary amine to afford novel crystalline lithium alkyls; a single-crystal X-ray structure determination of [{o-C₆H ₄(CHSiMe₃)₂}{Li(tmeda)}₂] shows each lithium to interact with both the α- and adjacent ring carbon atoms from opposite sides of the o-xylidene plane.

Original language	English
Pages (from-to)	14-15
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	1
DOIs	https://doi.org/10.1039/C39820000014
Publication status	Published - 1 Jan 1982
Externally published	Yes

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title = "Crystalline alkyl-lithiums from α-trimethylsilyl-substituted o-xylenes; x-ray crystal structure of [{o-C6H4(CHSiMe 3)2}{Li(tmeda)}2] (tmeda = Me 2NCH2CH2NMe2)",

abstract = "Reaction of [o-C6H4(CHRR′)(CHR″R‴) ] (R, R′, R″, R‴ = H or SiMe3) with LiBu n in n-hexane in the presence of Me2NCH2CH 2NMe2 (tmeda) or MeN(CH2CH2NMe 2)2 (pmdeta) results in selective lithiation of the α-carbon in a manner dependent on the nature of the associated substituents and the tertiary amine to afford novel crystalline lithium alkyls; a single-crystal X-ray structure determination of [{o-C6H 4(CHSiMe3)2}{Li(tmeda)}2] shows each lithium to interact with both the α- and adjacent ring carbon atoms from opposite sides of the o-xylidene plane.",

author = "Lappert, {Michael F.} and Raston, {Colin L.} and Skelton, {Brian W.} and White, {Allan H.}",

year = "1982",

month = jan,

day = "1",

doi = "10.1039/C39820000014",

language = "English",

pages = "14--15",

journal = "Journal of the Chemical Society, Chemical Communications",

issn = "0022-4936",

publisher = "Chemical Society",

number = "1",

}

Crystalline alkyl-lithiums from α-trimethylsilyl-substituted o-xylenes; x-ray crystal structure of [{o-C₆H₄(CHSiMe ₃)₂}{Li(tmeda)}₂] (tmeda = Me ₂NCH₂CH₂NMe₂). / Lappert, Michael F.; Raston, Colin L.; Skelton, Brian W. et al.
In: Journal of the Chemical Society, Chemical Communications, No. 1, 01.01.1982, p. 14-15.

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

TY - JOUR

T1 - Crystalline alkyl-lithiums from α-trimethylsilyl-substituted o-xylenes; x-ray crystal structure of [{o-C6H4(CHSiMe 3)2}{Li(tmeda)}2] (tmeda = Me 2NCH2CH2NMe2)

AU - Lappert, Michael F.

AU - Raston, Colin L.

AU - Skelton, Brian W.

AU - White, Allan H.

PY - 1982/1/1

Y1 - 1982/1/1

N2 - Reaction of [o-C6H4(CHRR′)(CHR″R‴) ] (R, R′, R″, R‴ = H or SiMe3) with LiBu n in n-hexane in the presence of Me2NCH2CH 2NMe2 (tmeda) or MeN(CH2CH2NMe 2)2 (pmdeta) results in selective lithiation of the α-carbon in a manner dependent on the nature of the associated substituents and the tertiary amine to afford novel crystalline lithium alkyls; a single-crystal X-ray structure determination of [{o-C6H 4(CHSiMe3)2}{Li(tmeda)}2] shows each lithium to interact with both the α- and adjacent ring carbon atoms from opposite sides of the o-xylidene plane.

AB - Reaction of [o-C6H4(CHRR′)(CHR″R‴) ] (R, R′, R″, R‴ = H or SiMe3) with LiBu n in n-hexane in the presence of Me2NCH2CH 2NMe2 (tmeda) or MeN(CH2CH2NMe 2)2 (pmdeta) results in selective lithiation of the α-carbon in a manner dependent on the nature of the associated substituents and the tertiary amine to afford novel crystalline lithium alkyls; a single-crystal X-ray structure determination of [{o-C6H 4(CHSiMe3)2}{Li(tmeda)}2] shows each lithium to interact with both the α- and adjacent ring carbon atoms from opposite sides of the o-xylidene plane.

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U2 - 10.1039/C39820000014

DO - 10.1039/C39820000014

M3 - Article

SN - 0022-4936

SP - 14

EP - 15

JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

IS - 1

ER -

Crystalline alkyl-lithiums from α-trimethylsilyl-substituted o-xylenes; x-ray crystal structure of [{o-C₆H₄(CHSiMe ₃)₂}{Li(tmeda)}₂] (tmeda = Me ₂NCH₂CH₂NMe₂)

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