The electrophilic cleavage of cyclopropylcarbinylstannanes. Confirmation of traylor's prediction.

Andrew J. Lucke; David J. Young

doi:10.1016/S0040-4039(00)74893-3

The electrophilic cleavage of cyclopropylcarbinylstannanes. Confirmation of traylor's prediction.

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Abstract

The reaction of cyclopropylcarbinyltrialkylstannanes (CPCSnR₃) 1a (R=Me) and 1b (R=Bu) with sulfur dioxide in chloroform or methanol yields the homoallylic tin sulphinates 2a and 2b respectively. The reaction of 1a with iodine in chloroform yields predominantly 4-iodo-1-butene (3) and trimethyltin iodide while in methanol the corresponding reaction yields CPCSnMe₂I (4) and methyl iodide.

Original language	English
Pages (from-to)	807-810
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	6
DOIs	https://doi.org/10.1016/S0040-4039(00)74893-3
Publication status	Published - 4 Feb 1991
Externally published	Yes

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title = "The electrophilic cleavage of cyclopropylcarbinylstannanes. Confirmation of traylor's prediction.",

abstract = "The reaction of cyclopropylcarbinyltrialkylstannanes (CPCSnR3) 1a (R=Me) and 1b (R=Bu) with sulfur dioxide in chloroform or methanol yields the homoallylic tin sulphinates 2a and 2b respectively. The reaction of 1a with iodine in chloroform yields predominantly 4-iodo-1-butene (3) and trimethyltin iodide while in methanol the corresponding reaction yields CPCSnMe2I (4) and methyl iodide.",

author = "Lucke, {Andrew J.} and Young, {David J.}",

year = "1991",

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doi = "10.1016/S0040-4039(00)74893-3",

language = "English",

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pages = "807--810",

journal = "Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry",

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AU - Lucke, Andrew J.

AU - Young, David J.

PY - 1991/2/4

Y1 - 1991/2/4

N2 - The reaction of cyclopropylcarbinyltrialkylstannanes (CPCSnR3) 1a (R=Me) and 1b (R=Bu) with sulfur dioxide in chloroform or methanol yields the homoallylic tin sulphinates 2a and 2b respectively. The reaction of 1a with iodine in chloroform yields predominantly 4-iodo-1-butene (3) and trimethyltin iodide while in methanol the corresponding reaction yields CPCSnMe2I (4) and methyl iodide.

AB - The reaction of cyclopropylcarbinyltrialkylstannanes (CPCSnR3) 1a (R=Me) and 1b (R=Bu) with sulfur dioxide in chloroform or methanol yields the homoallylic tin sulphinates 2a and 2b respectively. The reaction of 1a with iodine in chloroform yields predominantly 4-iodo-1-butene (3) and trimethyltin iodide while in methanol the corresponding reaction yields CPCSnMe2I (4) and methyl iodide.

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U2 - 10.1016/S0040-4039(00)74893-3

DO - 10.1016/S0040-4039(00)74893-3

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AN - SCOPUS:0026069570

VL - 32

SP - 807

EP - 810

JO - Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry

JF - Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry

SN - 0040-4039

IS - 6

ER -