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Communication | Regular issue | Vol 27, No. 7, 1988, pp.1595-1598
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4570
Exceptionally Facile Reduction of Carboxylic Acid Salts to Aldehydes by 9-Borabicyclo[3.3.1]nonane

Jin Soon Cha,* Se Yeon Oh, Kwang Woo Lee, Mal Sook Yoon, Jae Cheol Lee, and Jin Euog Kim

*Department of Chemistry, Yeungnam University, Kyongsan 712-749, Korea


Both sodium and lithium salts of carboxylic acids in the presence of 2 equiv of 9-borabicyclo[3.3.linonane(9-BBN) are readily converted to the aldehydes in approximately 1-3 h at room temperature in high yields. Thus, simple aliphatic carboxylic acid salts, such as butyric, hexanoic, decanoic, stearic, isobutyric, isopentanoic, pivalic, cyclopropanecarboxylic, and cyclohexanecarboxylic acid salts, readily undergo the reaction to aldehydes in yields of 84-99%. Derivative, such as diphenylacetic acid salts, undergoes the reaction in a h s t quantitative yields. Even dicarboxylic acid salts, such as α-camphoric and 1,10-decanedicarboxyilc acid salts, work equally well. The yields of aromatic carboxylic acid salts are variable ranged from 54 to 83% except for the case of terephthalic acid salts being 99%.