Application of Copper(I)-Induced Thiophenoxide Removal to Ring Expansions or Chain Extensions of Aldehydes and Ketones. Detection, Isolation, and Independent Preparation of the α-Epoxy Thioether Intermediate

Theodore Cohen; David Kuhn; J R Falck

doi:10.1021/ja00849a045

Application of Copper(I)-Induced Thiophenoxide Removal to Ring Expansions or Chain Extensions of Aldehydes and Ketones. Detection, Isolation, and Independent Preparation of the α-Epoxy Thioether Intermediate

Theodore Cohen, David Kuhn, J R Falck

Biochemistry

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

84 Scopus citations

Abstract

Recent work from this laboratory¹ has demonstrated that sulfur-stabilized carbonium ions can be readily generated in organic solvents under mild conditions by removal of a thiophenoxide ion from a thioacetal or thioketal using soluble cuprous trifluoromethanesulfonate (triflate).² The procedure was applied to the syntheses of a variety of vinyl sulfides and of a furan. We now report applications which result in new synthetic procedures and which illustrate the high selectivity of the process.

Original language	English (US)
Pages (from-to)	4749-4751
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	97
Issue number	16
DOIs	https://doi.org/10.1021/ja00849a045
State	Published - Aug 1 1975

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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Application of Copper(I)-Induced Thiophenoxide Removal to Ring Expansions or Chain Extensions of Aldehydes and Ketones. Detection, Isolation, and Independent Preparation of the α-Epoxy Thioether Intermediate. / Cohen, Theodore; Kuhn, David; Falck, J R.
In: Journal of the American Chemical Society, Vol. 97, No. 16, 01.08.1975, p. 4749-4751.

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

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Application of Copper(I)-Induced Thiophenoxide Removal to Ring Expansions or Chain Extensions of Aldehydes and Ketones. Detection, Isolation, and Independent Preparation of the α-Epoxy Thioether Intermediate

Abstract

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