The regiochemistry of cyclopropylcarbinylstannane ring fission

Andrew J. Lucke; David J. Young

doi:10.1016/S0040-4039(00)76771-2

The regiochemistry of cyclopropylcarbinylstannane ring fission

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

Abstract

The reaction of 2-methylcyclopropylcarbinyltrimethylstannane 1 in chloroform with the electrophiles sulphur dioxide, trifluoroacetic acid, and iodine proceeds preferentially with ring cleavage and addition at the unsubstituted cyclopropyl methylene. Iodination and acidolysis in methanol proceeds exclusively with tin-methyl bond cleavage.

Original language	English
Pages (from-to)	1609-1612
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4039(00)76771-2
Publication status	Published - 7 Mar 1994
Externally published	Yes

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10.1016/S0040-4039(00)76771-2

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title = "The regiochemistry of cyclopropylcarbinylstannane ring fission",

abstract = "The reaction of 2-methylcyclopropylcarbinyltrimethylstannane 1 in chloroform with the electrophiles sulphur dioxide, trifluoroacetic acid, and iodine proceeds preferentially with ring cleavage and addition at the unsubstituted cyclopropyl methylene. Iodination and acidolysis in methanol proceeds exclusively with tin-methyl bond cleavage.",

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

year = "1994",

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AU - Lucke, Andrew J.

AU - Young, David J.

PY - 1994/3/7

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N2 - The reaction of 2-methylcyclopropylcarbinyltrimethylstannane 1 in chloroform with the electrophiles sulphur dioxide, trifluoroacetic acid, and iodine proceeds preferentially with ring cleavage and addition at the unsubstituted cyclopropyl methylene. Iodination and acidolysis in methanol proceeds exclusively with tin-methyl bond cleavage.

AB - The reaction of 2-methylcyclopropylcarbinyltrimethylstannane 1 in chloroform with the electrophiles sulphur dioxide, trifluoroacetic acid, and iodine proceeds preferentially with ring cleavage and addition at the unsubstituted cyclopropyl methylene. Iodination and acidolysis in methanol proceeds exclusively with tin-methyl bond cleavage.

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U2 - 10.1016/S0040-4039(00)76771-2

DO - 10.1016/S0040-4039(00)76771-2

M3 - Article

AN - SCOPUS:0028273579

VL - 35

SP - 1609

EP - 1612

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 - 10

ER -

The regiochemistry of cyclopropylcarbinylstannane ring fission

Abstract

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