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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 9, Number 1
BKCSDE 9(1)
January 20, 1988

Title	Direct Transformation of Carboxylic Acids into Aldehydes through Acyloxy-9-borabicyclo[3.3.1]nonane
Author	Jin Soon Cha*, Se Yeon Oh, Kwang Woo Lee, Mal Sook Yoon, Jae Cheol Lee, Jin Euog Kim
Keywords
Abstract	New methods for the direct reduction of carboxylic acids to aldehydes through the treatments of B-acyloxy-9-borabicyclo[3.3.1]nonane (acyloxy-9-BBN) with tert-butyllithium and 9-borabicyclo[3.3.1]nonane or with lithium 9-boratabicyclo[3.3.1]nonane (Li 9-BBNH) are described. Both these systems provide the corresponding aldehydes from various carboxylic acids in high yields. A mechanism for the recuction through stepwise treatment of acyloxy-9-BBN with tert-butylithium and 9-BBN, which seems to involve the hydride migration through 9-BBN, is proposed and discussed in connection with the reduction through treatment of acyloxy-9-BBN with Li 9-BBNH.
Page	48 - 52
Full Text	PDF

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