Metalation reactions-XIV. The generality of the 1.3-Sigmatropic shift of hydrogen in allenyllithium compounds

J. Klein; J. Y. Becker

doi:10.1016/S0040-4020(01)93861-X

Metalation reactions-XIV. The generality of the 1.3-Sigmatropic shift of hydrogen in allenyllithium compounds

J. Klein
, J. Y. Becker

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

49 Scopus citations

Abstract

Dimetalation of aliphatic 2-alkynes was observed in mild conditions in ether solution. Only 2-butyne has undergone monometalation exclusively. The dilithio compounds of 1- and 2-alkynes were attacked by electrophiles first at the 3-position. A 1.3-sigmatropic shift occurred in the monolithioallenes to give terminal acetylides. Metalation of 3-alkyne gave only a monolithiated compound in the conditions studied.

Original language	English
Pages (from-to)	5385-5392
Number of pages	8
Journal	Tetrahedron
Volume	28
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4020(01)93861-X
State	Published - 1 Jan 1972
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)93861-X

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title = "Metalation reactions-XIV. The generality of the 1.3-Sigmatropic shift of hydrogen in allenyllithium compounds",

abstract = "Dimetalation of aliphatic 2-alkynes was observed in mild conditions in ether solution. Only 2-butyne has undergone monometalation exclusively. The dilithio compounds of 1- and 2-alkynes were attacked by electrophiles first at the 3-position. A 1.3-sigmatropic shift occurred in the monolithioallenes to give terminal acetylides. Metalation of 3-alkyne gave only a monolithiated compound in the conditions studied.",

author = "J. Klein and Becker, \{J. Y.\}",

year = "1972",

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doi = "10.1016/S0040-4020(01)93861-X",

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T1 - Metalation reactions-XIV. The generality of the 1.3-Sigmatropic shift of hydrogen in allenyllithium compounds

AU - Klein, J.

AU - Becker, J. Y.

PY - 1972/1/1

Y1 - 1972/1/1

N2 - Dimetalation of aliphatic 2-alkynes was observed in mild conditions in ether solution. Only 2-butyne has undergone monometalation exclusively. The dilithio compounds of 1- and 2-alkynes were attacked by electrophiles first at the 3-position. A 1.3-sigmatropic shift occurred in the monolithioallenes to give terminal acetylides. Metalation of 3-alkyne gave only a monolithiated compound in the conditions studied.

AB - Dimetalation of aliphatic 2-alkynes was observed in mild conditions in ether solution. Only 2-butyne has undergone monometalation exclusively. The dilithio compounds of 1- and 2-alkynes were attacked by electrophiles first at the 3-position. A 1.3-sigmatropic shift occurred in the monolithioallenes to give terminal acetylides. Metalation of 3-alkyne gave only a monolithiated compound in the conditions studied.

UR - https://www.scopus.com/pages/publications/0041005909

U2 - 10.1016/S0040-4020(01)93861-X

DO - 10.1016/S0040-4020(01)93861-X

M3 - Article

AN - SCOPUS:0041005909

SN - 0040-4020

VL - 28

SP - 5385

EP - 5392

JO - Tetrahedron

JF - Tetrahedron

IS - 21

ER -

Metalation reactions-XIV. The generality of the 1.3-Sigmatropic shift of hydrogen in allenyllithium compounds

Abstract

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