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Synlett 1991; 1991(10): 712-714
DOI: 10.1055/s-1991-34771
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A New Approach to the Synthesis of 2-Aza-1,3-Dienes through a Novel 1,4-Rearrangement of a Trimethylsilyl Group from Nitrogen to Carbon

A. Degl'lnnocenti* , A. Mordini, D. Pinzani, G. Reginato, A. Ricci
  • *Centro CNR Composti Eterociclici c / o Dipartimento di Chimica Organica "U. Schiff". via G. Capponi 9,I-50121 Firenze, Italy
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Publication Date:
13 March 2002 (online)

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The metalation of N,N,3-tris(trimethylsilyl)-2-propen-1-amine (1) with the equimolar mixture butyllithium/diisopropylamine/potassium tert-butoxide, followed by quenching with aldehydes or ketones, leads to substituted 2-aza-1,3- dienes (N-alkylidene-3,3-bis(trimethylsilyl)-1-propen-1-amines) in satisfactory yield through a novel N → C 1,4-rearrangement of a trimethylsilyl group.