Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Mechanism of the Base-Promoted Rearrangement of N,N-Dichlorocyclohexylamine to 2-Aminocyclohexanone and the Deaminative Diazotization of 2-Aminocyclohexanone
Mamoru NakaiNaomichi FurukawaShigeru Oae
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1969 Volume 42 Issue 10 Pages 2917-2920


N,N-Dichlorocyclohexylamine-1-14C has been treated with sodium methoxide in methanol and then with hydrochloric acid to yield 14C-labeled 2-aminocyclohexanone hydrochloride. Successive degradations have revealed that practically all the 14C activity was found in the carbonyl carbon of the original aminoketone. From the 14C distribution, it has been concluded that the reaction is essentially the same as that proposed for the Neber rearrangement. As a part of the degradation of 2-aminocyclohexanone, deaminative diazotization was employed to obtain cyclopentanecarboxylic acid together with other minor products. The 14C tracer work revealed that the carbonyl group of the acid is originated from the carbonyl group of the 2-amino-ketone.

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