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

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56 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

Bibliographical note

Funding Information:
dideoxy-D-glucose3 0 (40 mg. 0.31 mmol), chlorotrlmethylsilan(e0 .31m L, 2.4 mmol), and trlethylamine (0.5 mL, 3.6 mmol) in benzene( 3 mL) was stirredf or 12 h at roomt emperatureA. fter evaporationo f the volatilec ompounds the residuew asp urifiedb y columnc hromatographoyn silica gel elutingw ith CH2Cl2t c give 37 mg( 60%)o f 37: oil; [a% = -70’ (c 0.6, CH2Cl2);1 HN MR (CDCl3) 6 0.09( s, 9 I-I), 1.62-2.23(m , 4 H), 3.69( dd,J = 6,6 Hz, 1 I-I), 3.98-4.10(m , 1 H), 4.38( d, J = 6 Hz, 1 I-I), 4.41-4.50( m, 1 I-I), 5.52( s, 1 H); 1X! NMR (CDQ3) 6 -0.07,37.6,39.1,63.1,67.5,71.7, 100.3.A nal. Calcdf or C9HisOsSi: C, 53.46;H , 8.91. Found:C , 53.53;H , 8.92. Acknowledgementsz We thankt heN IH andt heS chering-PlougCho rporationfo r financial support Dr. Doo Ok Jang wasa Schering-PlougShc holar.

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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

@article{f146b18f294a4ccdbe71888bebc8f556,

title = "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",

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.",

author = "Barton, {Derek H.R.} and Jang, {Doo Ok} and Jaszberenyi, {Joseph Cs}",

note = "Funding Information: dideoxy-D-glucose3 0 (40 mg. 0.31 mmol), chlorotrlmethylsilan(e0 .31m L, 2.4 mmol), and trlethylamine (0.5 mL, 3.6 mmol) in benzene( 3 mL) was stirredf or 12 h at roomt emperatureA. fter evaporationo f the volatilec ompounds the residuew asp urifiedb y columnc hromatographoyn silica gel elutingw ith CH2Cl2t c give 37 mg( 60%)o f 37: oil; [a% = -70{\textquoteright} (c 0.6, CH2Cl2);1 HN MR (CDCl3) 6 0.09( s, 9 I-I), 1.62-2.23(m , 4 H), 3.69( dd,J = 6,6 Hz, 1 I-I), 3.98-4.10(m , 1 H), 4.38( d, J = 6 Hz, 1 I-I), 4.41-4.50( m, 1 I-I), 5.52( s, 1 H); 1X! NMR (CDQ3) 6 -0.07,37.6,39.1,63.1,67.5,71.7, 100.3.A nal. Calcdf or C9HisOsSi: C, 53.46;H , 8.91. Found:C , 53.53;H , 8.92. Acknowledgementsz We thankt heN IH andt heS chering-PlougCho rporationfo r financial support Dr. Doo Ok Jang wasa Schering-PlougShc holar.",

year = "1993",

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doi = "10.1016/S0040-4020(01)87198-2",

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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 › peer-review

TY - JOUR

T1 - The invention of radical reactions. Part XXXI. Diphenylsilane

T2 - a reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry

AU - Barton, Derek H.R.

AU - Jang, Doo Ok

AU - Jaszberenyi, Joseph Cs

N1 - Funding Information: dideoxy-D-glucose3 0 (40 mg. 0.31 mmol), chlorotrlmethylsilan(e0 .31m L, 2.4 mmol), and trlethylamine (0.5 mL, 3.6 mmol) in benzene( 3 mL) was stirredf or 12 h at roomt emperatureA. fter evaporationo f the volatilec ompounds the residuew asp urifiedb y columnc hromatographoyn silica gel elutingw ith CH2Cl2t c give 37 mg( 60%)o f 37: oil; [a% = -70’ (c 0.6, CH2Cl2);1 HN MR (CDCl3) 6 0.09( s, 9 I-I), 1.62-2.23(m , 4 H), 3.69( dd,J = 6,6 Hz, 1 I-I), 3.98-4.10(m , 1 H), 4.38( d, J = 6 Hz, 1 I-I), 4.41-4.50( m, 1 I-I), 5.52( s, 1 H); 1X! NMR (CDQ3) 6 -0.07,37.6,39.1,63.1,67.5,71.7, 100.3.A nal. Calcdf or C9HisOsSi: C, 53.46;H , 8.91. Found:C , 53.53;H , 8.92. Acknowledgementsz We thankt heN IH andt heS chering-PlougCho rporationfo r financial support Dr. Doo Ok Jang wasa Schering-PlougShc holar.

PY - 1993/8/13

Y1 - 1993/8/13

N2 - 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.

AB - 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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U2 - 10.1016/S0040-4020(01)87198-2

DO - 10.1016/S0040-4020(01)87198-2

M3 - Article

AN - SCOPUS:0027291622

VL - 49

SP - 7193

EP - 7214

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 33

ER -

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

Abstract

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