The Zn/AcOH reduction of 1 leads only to the carbonyl reduction, while C-decyanation occurs in the case of 2. The mechanism of the latter reaction is discussed. The N-decyanation of N-cyanoamines 3 and 4 involves an ionic mechanism, leading to N-acyl derivatives and isocyanic acid, the latter compound being ultimately reduced to formic acid.
DI VONA, M.l., Luchetti, L., Rosnati, V. (1994). Zinc-promoted reactions. 9. The fate of the cyano group in the reduction of simple cyanoketones and N-cyanoamines. TETRAHEDRON, 50(27), 8203-8208 [10.1016/S0040-4020(01)85302-3].
Zinc-promoted reactions. 9. The fate of the cyano group in the reduction of simple cyanoketones and N-cyanoamines
DI VONA, MARIA LUISA;LUCHETTI, LUCIANA;ROSNATI, VITTORIO
1994-01-01
Abstract
The Zn/AcOH reduction of 1 leads only to the carbonyl reduction, while C-decyanation occurs in the case of 2. The mechanism of the latter reaction is discussed. The N-decyanation of N-cyanoamines 3 and 4 involves an ionic mechanism, leading to N-acyl derivatives and isocyanic acid, the latter compound being ultimately reduced to formic acid.File in questo prodotto:
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