Stereospecific and regioselective isocyanide insertions into siliranes and reactions of the resulting iminosilacyclobutanes

Phuc T. Nguyen, Wylie S. Palmer, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

The insertions of p-tolyl and tert-butyl isocyanide into siliranes yielded iminosilacyclobutanes with stereospecific retention of configuration. Monosubstituted siliranes underwent insertion into the more substituted Si-C bond of the ring, although this regioselectivity was eroded as substitution increased on the silirane ring. The iminosilacyclobutane products tautomerized thermally or in the presence of a palladium catalyst to yield the thermodynamically more stable aminosilacyclobutenes. Ring-expansion reactions of iminosilacyclobutanes were promoted by acids: treatment with aqueous copper sulfate produced an oxasilacyclopentane in high yield, whereas with trifluoroacetic acid, oxasilacyclohexanes were formed.

Original languageEnglish (US)
Pages (from-to)1843-1848
Number of pages6
JournalJournal of Organic Chemistry
Volume64
Issue number6
DOIs
StatePublished - Mar 19 1999

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Copper Sulfate
Trifluoroacetic Acid
Regioselectivity
Palladium
Cyanides
Substitution reactions
Catalysts
Acids
tert-butyl isocyanide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stereospecific and regioselective isocyanide insertions into siliranes and reactions of the resulting iminosilacyclobutanes. / Nguyen, Phuc T.; Palmer, Wylie S.; Woerpel, Keith.

In: Journal of Organic Chemistry, Vol. 64, No. 6, 19.03.1999, p. 1843-1848.

Research output: Contribution to journalArticle

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