Wittig‐Reaktionen mit Cyanhydrinen sowie Redoxreaktion des 4‐Nitromandelsäurenitrils | Zendy

Koßmehl Gerhard | Zendy; Nuck Rolf | Zendy

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Wittig‐Reaktionen mit Cyanhydrinen sowie Redoxreaktion des 4‐Nitromandelsäurenitrils

Author(s) -

Koßmehl Gerhard,

Nuck Rolf

Publication year - 1981

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19811140822

Subject(s) - wittig reaction , chemistry , aldehyde , redox , yield (engineering) , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy

Wittig Reactions of Cyanohydrines and Redox Reaction of 4‐Nitromandelonitrile Substitued mandelonitriles 5 (R 1 H, OCH 3 , NO 2 ) react in the presence of sodium tert ‐ butoxide as a base like the corresponding aldehydes with substituted benzylidenetriphenylphosphoranes via the Wittig reaction to yield 4,4′‐disubstituted stilbenes 8 , for which the ( E )/( Z ) stereoisomer ratios are given. Our results refer to a reaction with a preceding cyanohydrine‐aldehyde equilibrium. 4‐Nitromandelonitrile (5a) forms in a basic methanolic solution via a redox reaction a mixture of dimethyl 4,4′‐azoxybenzenedicarboxylate (11) and methyl 4‐nitrobenzoate (12) .

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