Selective Reductions. XIX. The Rapid Reaction of Carboxylic Acids with Borane-Tetrahydrofuran. A Remarkably Convenient Procedure for the Selective Conversion of Carboxylic Acids to the Corresponding Alcohols in the Presence of Other Functional Groups

Journal of Organic Chemistry

Volumn 38, Issue 16, 1973, Pages 2786-2792

  Yoon, Nung Min ^a   Pak, Chwang Siek ^a   Brown, Herbert C ^b   Krishnamurthy, S ^b   Stocky, Thomas P ^b  

^a Sogang University   (South Korea)

^b PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85022241083     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00956a011     Document Type: Article

References (40)

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29. Hydrogen evolution is instantaneous and quantitative even at -20°, indicating the remarkable ease with which triacyloxyboranes are formed. Recently, it has been reported that the triaryloxyboranes initially formed can undergo dismutation to acid anhydrides and oxybisdiacyloxy-boranes and the resulting dismuted products undergo further reduction with borane-THF to the alcohol stage; see A. Pelter, M. G. Hutchings, T. E. Levitt, and K. Smith, Chem. Commun., 347 (1970). However, the rates of reduction of carboxylic acids observed in the present study are far faster than the rates of dismutfttion for triacyloxyboranes in the majority of instances. This indicates that dismutation need not be an important factor in the presence of excess borane-THF.
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