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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 10, Number 1
BKCSDE 10(1)
January 20, 1989 

Reduction of Tertiary Amides with Borane in the Presence of Trimethyl Borate
In Hwan Oh, Nung Min Yoon*, Young Soo Gyoung
Various tertiary amides have been subjected to the reduction by borane-THF in the presence of trimethyl borate at 0℃ and the product ratio of alcohol and amine have been analyzed in order to find out the possible way to obtain one product exclusively on the basis of the structure of amides. In the case of N,N-dimethyl derivatives of both linear aliphatic and aromatic amides the corresponding alcohols were produced predominantly. However, the bulkier tertiary amides such as N,N-diethyl and hindered acid derivatives afforded amines rather than alcohols. The mechanism of borane reduction of tertiary amides is also discussed.
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