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Título

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

AutorCarrau, Reyes; Hernández, Rosendo ; Suárez, Ernesto ; Betancor, Carmen
Fecha de publicación1987
EditorRoyal Society of Chemistry (Great Britain)
CitaciónJournal of the Chemical Society - Perkin Transactions 1987: 937-943 (1987)
ResumenPhotolysis 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.
Descripción7 pages, 1 table, 2 schemes.
Versión del editorhttp://dx.doi.org/10.1039/P19870000937
URIhttp://hdl.handle.net/10261/17583
DOI10.1039/P19870000937
ISSN1472-7781
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