Formaldehyde dimethylhydrazone: A new neutral reagent for nucleophilic hydroformylation and hydrocyanation

JM Lassaletta, R Fernández, C Gasch, J Vázquez

Index: Lassaletta, Jose-Maria; Fernandez, Rosario; Gasch, Consolacion; Vazquez, Juan Tetrahedron, 1996 , vol. 52, # 27 p. 9143 - 9160

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Citation Number: 31

Abstract

The readily available title compound smoothly adds to nitroolefins without any need of base or catalysis, giving β-nitrodimethylhydrazones 3 in high yields. Michael adducts 3 have been successfully transformed into β-nitroaldehydes by ozonolysis and in β-nitronitriles in excellent yields by treatment with MMPP. Therefore, formaldehyde dimethylhydrazone behaves as a new neutral formyl anion and cyanide equivalent, introducing a ...