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

Andrew J. Lucke, David J. Young

Research output: Contribution to journalArticleResearchpeer-review

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 languageEnglish
Pages (from-to)807-810
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number6
DOIs
Publication statusPublished - 4 Feb 1991
Externally publishedYes

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Chloroform
Methanol
Sulfur Dioxide
Tin
Iodides
Iodine
1-butene
trimethyltin
methyl iodide

Cite this

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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.",
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The electrophilic cleavage of cyclopropylcarbinylstannanes. Confirmation of traylor's prediction. / Lucke, Andrew J.; Young, David J.

In: Tetrahedron Letters, Vol. 32, No. 6, 04.02.1991, p. 807-810.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Young, David J.

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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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