alpha,beta-Unsaturated hydrazones can be easily converted into N-allyl hydrazines by reaction with dimethylamine-borane/p-toluenesulfonic acid under mild reaction conditions. The reduction works well for N'-allyhydrazides but N'-allyl-N,N-dimethylhydrazines are rapidly reoxidised by air and so need to be manipulated under an inert atmosphere prior to M-acylation. Competitive conjugate reduction can also be observed and the regioselectivity of the dimethylamine-borane attack is determined by steric and/or electronic factors. The procedure is also effective for the C=N reduction of unconjugated hydrazones. (C) 2002 Elsevier Science Ltd. All rights reserved.

1,2-reduction of alpha,beta-unsaturated hydrazones using dimethylamine-borane/p-toluenesulfonic acid: an easy route to allyl hydrazines / M. E., Casarini; Ghelfi, Franco; Libertini, Emanuela; Pagnoni, Ugo Maria; A. F., Parsons. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 58:(2002), pp. 7925-7932.

1,2-reduction of alpha,beta-unsaturated hydrazones using dimethylamine-borane/p-toluenesulfonic acid: an easy route to allyl hydrazines

GHELFI, Franco;LIBERTINI, Emanuela;PAGNONI, Ugo Maria;
2002

Abstract

alpha,beta-Unsaturated hydrazones can be easily converted into N-allyl hydrazines by reaction with dimethylamine-borane/p-toluenesulfonic acid under mild reaction conditions. The reduction works well for N'-allyhydrazides but N'-allyl-N,N-dimethylhydrazines are rapidly reoxidised by air and so need to be manipulated under an inert atmosphere prior to M-acylation. Competitive conjugate reduction can also be observed and the regioselectivity of the dimethylamine-borane attack is determined by steric and/or electronic factors. The procedure is also effective for the C=N reduction of unconjugated hydrazones. (C) 2002 Elsevier Science Ltd. All rights reserved.
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1,2-reduction of alpha,beta-unsaturated hydrazones using dimethylamine-borane/p-toluenesulfonic acid: an easy route to allyl hydrazines / M. E., Casarini; Ghelfi, Franco; Libertini, Emanuela; Pagnoni, Ugo Maria; A. F., Parsons. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 58:(2002), pp. 7925-7932.
M. E., Casarini; Ghelfi, Franco; Libertini, Emanuela; Pagnoni, Ugo Maria; A. F., Parsons
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/310357
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