Exceptionally Facile Reduction of Carboxylic Acid Salts to Aldehydes by 9-Borabicyclo[3.3.1]nonane
1988; Elsevier BV; Volume: 27; Issue: 7 Linguagem: Inglês
10.3987/com-88-4570
ISSN1881-0942
AutoresJin Soon, Se Yeon Oh, Kwang Woo Lee, M. S. YOON, Jae Cheol Lee, Jin Euog Kim,
Tópico(s)Chemical Synthesis and Analysis
ResumoBath sodium and lithium salts of carboxylic acids in t h e presence of 2 equiv of 9-borabicycl0[3.3.Unonane(9-BBN) x.2 readily converted t o the aldehydes i n a p p m x h t e l y 1-3 h a t m o m t e m p e r a t m in high yields.Thus, simple a l i p h a t i c carboxyllc acld s a l t s , such a s butyric, hexanoic, decanoic, s t e a r i c , isobutyric, isopentanoic, pivalic, cyclopmpanecarboxylic, and cyclohexanecarboxylic acid salts, readily undergo the reaction t o aldehydes in ylelds of 84-995.Derivative, such a s diphenylacetic acid salts, undergoes the reaction in a h s t quantitative yields.Even dicarboxylic acid s a l t s , such a s a-canphoric and 1,lO-decanedicarboxyllc acid salts, work equally well.The yields of arorratic camoxylic acid salts are variable r a n a d from
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