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Synthesis 1991; 1991(3): 225-228
DOI: 10.1055/s-1991-26428
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The Reaction of Arylaldehydes with Hexamethylphosphorous Triamide and the Use of the Resulting Products for the Synthesis of Enamines and Deoxybenzoins

Francesco Babudri* , Vito Fiandanese, Roberta Musio, Francesco Naso, Oronzo Sciavovelli, Antonio Scilimati
  • *Centro C.N.R. di Studio sulle Metodologie Innovative di Sintesi Organiche, Dipartimento di Chimica, Università di Bari, via Amendola 173, I-70126 Bari, Italy
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Publication Date:
17 September 2002 (online)

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The reaction between the arylaldehydes 1a,b and hexamethylphosphorous triamide 2 leads to the [aryl(dimethylamino)methyl]phosphonic bis(dimethylamides) 3a,b. These can be easily deprotonated by butyllithium in 1,2-dimethoxyethane and condensed with arylaldehydes to afford enamines 4a-f or deoxybenzoins 5a-f in fair to good yield.

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