Tetrahedron

Synthesis of α-phenylselanyl and α-phenylsulfanyl nitriles from aldehyde N, N-dialkylhydrazones

M Ternon, X Pannecoucke, F Outurquin, C Paulmier

Index: Ternon, Michael; Pannecoucke, Xavier; Outurquin, Francis; Paulmier, Claude Tetrahedron, 2002 , vol. 58, # 16 p. 3275 - 3279

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Citation Number: 3

Abstract

Phenylselenenylation of azaenolates, formed by LDA treatment of dimethylhydrazones 1 (R2= H) and derived from linear aliphatic aldehydes, has led to α-phenylselanyl hydrazones 2. α-Phenylselanyl nitriles 3 were, however, isolated when an excess of base and of PhSeX (X= Cl, Br) were used. Hydrazones 1 bearing an α-alkyl substituent (R2≠ H) gave also nitriles 3. SAMP-hydrazones 4 showed the same reactivity and the corresponding nitriles ...