Direct synthesis of. alpha.,. beta.-unsaturated nitriles from acetonitrile and carbonyl compounds: survey, crown effects, and experimental conditions

SA DiBiase, BA Lipisko, A Haag…

Index: DiBiase,S.A. et al. Journal of Organic Chemistry, 1979 , vol. 44, # 25 p. 4640 - 4649

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Citation Number: 73

Abstract

Solvent. Determined by GLC and/or NMR (see Experimental Section for details). 44% of 3- nitrobenzyl alcohol obtained when the reaction was conducted at 25" C; at reflux, only tar was isolated. e 2 equivs of KOH used. Yield lower on 0.5 mol scale. JI Cannizzaro re-strate) nitrile. The dehydration occurs more readily in polar (acetonitrile, t I-391) and in protic than in nonpolar (eg, THF, t= 7.611) aprotic solution, an observation which has ample precedent ...

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