Issue 0, 1987
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Intramolecular functionalization of N-cyanamide radicals: synthesis of 1,4-and 1,5-N-cyanoepimino compounds

Reyes Carrau,   Rosendo Hernández,   Ernesto Suárez  and  Carmen Betancor  

Abstract

Photolysis of 3β-methoxymethoxy-5α-cholestan-6β-ylcyanamide (6), 29-methoxyfriedelan-3β-yl-cyanamide (15), (22R,25R)-5α-furostan-26-ylcyanamide (23), 8α,12-(12R/12S)-epoxylabdan-15-ylcyanamides, (32) and (33), in the presence of iodine and lead tetra-acetate leads to neutral cyanimyl radicals which undergo intramolecular hydrogen abstraction to produce N-cyanoepimino compounds. Better results are obtained with the system iodine and diacetoxyiodobenzene. The starting cyanamides have been prepared by reduction of the oximes (3) and (13) and of the amides (20), (28), and (29), respectively, with lithium aluminium hydride followed by cyanation with cyanogen bromide or with sodium cyanate and subsequent dehydration of the urea derivative with methanesulphonyl chloride.

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Article information

DOI
https://doi.org/10.1039/P19870000937
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1987, 937-943

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Intramolecular functionalization of N-cyanamide radicals: synthesis of 1,4-and 1,5-N-cyanoepimino compounds

R. Carrau, R. Hernández, E. Suárez and C. Betancor, J. Chem. Soc., Perkin Trans. 1, 1987, 937 DOI: 10.1039/P19870000937

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