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

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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 languageEnglish
Pages (from-to)7193-7214
Number of pages22
JournalTetrahedron
Volume49
Issue number33
DOIs
Publication statusPublished - 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.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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