A new approach to the synthesis of 2-aza-1,3-dienes through a novel 1,4 rearrangment of a trimethylsilyl group from nitrogen to carbon

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