The invention of radical reactions. Part XXXI. Diphenylsilane: a reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry

Derek H.R. Barton; Doo Ok Jang; Joseph Cs Jaszberenyi

doi:10.1016/S0040-4020(01)87198-2

The invention of radical reactions. Part XXXI. Diphenylsilane: a reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry

Derek H.R. Barton, Doo Ok Jang, Joseph Cs Jaszberenyi

Chemistry and Medical Chemistry

Research output: Contribution to journal › Article

53 Citations (Scopus)

Abstract

Various thionocarbonates and xanthates of alcohols and bis-xanthates of vic-diols are readily deoxygenated to the corresponding hydrocarbons or olefins, while bromides and iodides are dehalogenated with diphenylphenylsilane in good yield.

Original language	English
Pages (from-to)	7193-7214
Number of pages	22
Journal	Tetrahedron
Volume	49
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4020(01)87198-2
Publication status	Published - 1993 Aug 13

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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Barton, D. H. R., Jang, D. O., & Jaszberenyi, J. C. (1993). The invention of radical reactions. Part XXXI. Diphenylsilane: a reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry. Tetrahedron, 49(33), 7193-7214. https://doi.org/10.1016/S0040-4020(01)87198-2

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abstract = "Various thionocarbonates and xanthates of alcohols and bis-xanthates of vic-diols are readily deoxygenated to the corresponding hydrocarbons or olefins, while bromides and iodides are dehalogenated with diphenylphenylsilane in good yield.",

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Barton, DHR, Jang, DO & Jaszberenyi, JC 1993, 'The invention of radical reactions. Part XXXI. Diphenylsilane: a reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry', Tetrahedron, vol. 49, no. 33, pp. 7193-7214. https://doi.org/10.1016/S0040-4020(01)87198-2

The invention of radical reactions. Part XXXI. Diphenylsilane : a reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry. / Barton, Derek H.R.; Jang, Doo Ok; Jaszberenyi, Joseph Cs.

In: Tetrahedron, Vol. 49, No. 33, 13.08.1993, p. 7193-7214.

Research output: Contribution to journal › Article

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Barton DHR, Jang DO, Jaszberenyi JC. The invention of radical reactions. Part XXXI. Diphenylsilane: a reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry. Tetrahedron. 1993 Aug 13;49(33):7193-7214. https://doi.org/10.1016/S0040-4020(01)87198-2