N-silyl derivatives of cyclic secondary amines
Iodosilane reacts with pyrrolidine and with piperidine to give N-silylpyrrolidine and N-silylpiperidine in good yield. Physical properties of these new compounds are reported and discussed. Both form rather weak 1 : 1 adducts with trimethylborane, that of SiH3·NC5H10 being more readily dissociated; their 1 : 1 adducts with iodosilane are solids at room temperature. The Si–N bond is cleaved by hydrogen chloride at room temperature, although the intermediate complex SiH3·NC5H10,2HCl can be isolated at –88°. Pyrolysis of both compounds gives chiefly silane and SiH2(NCnH2n)2(n= 4 or 5). Attempts to prepare N-silylaziridine and NN′-disilylpiperazine by several routes are described.