THERMAL REARRANGEMENT OF N-SILYLMETHYLATED AZADIENES TO N-SILYLATED 2-PYRROLINES

Article abstract of DOI:10.1016/S0040-4039(00)93436-1

N-Silylmethylated 1-azadienes thermally rearranged to N-silylated 2-pyrrolines, which were readily hydrolyzed to 1-pyrrolines on workup.Formation of the N-silylated pyrrolines strongly suggested that the intramlecular cyclization proceeded via a 1,3-dipolar intermediate formed by the thermal 1,2-shift of the silyl group onto the nitrogen atom of the azadienes.