The regiochemistry of cyclopropylcarbinylstannane ring fission

Andrew J. Lucke, David J. Young

Research output: Contribution to journalArticleResearchpeer-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 languageEnglish
Pages (from-to)1609-1612
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number10
DOIs
Publication statusPublished - 7 Mar 1994
Externally publishedYes

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Trifluoroacetic Acid
Sulfur Dioxide
Tin
Halogenation
Chloroform
Iodine
Methanol

Cite this

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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.",
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The regiochemistry of cyclopropylcarbinylstannane ring fission. / Lucke, Andrew J.; Young, David J.

In: Tetrahedron Letters, Vol. 35, No. 10, 07.03.1994, p. 1609-1612.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Young, David J.

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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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