Bruce A. Ashby

Preparation, chemistry and spectra of (silylmethyl)-pyrroles

Abstract The compounds, RCH2Si(CH3)x[O(C2H5)]3-x, where x = 0, 1, 2, 3 and R = 1-pyrrolyl, were prepared. RCH2Si(CH3)3 was cleaved in alcoholic base by the same mode as C6H5CH2Si(CH2)3 but to a lesser degree. The failure of RSi(CH3)3 to rearrange thermally (650°) was confirmed; RCH2Si(CH3)3 rearranged (550°) to the 2-pyrrolyl isomer whose structure was determined by N-methylation and comparison with 1-methyl-2-(trimethylsilylmethyl)pyrrole prepared by an alternate path. Lithiation of 1-methylpyrrole followed by reaction with (1) chlorotrimethylsilane gave 1-methyl-2-(trimethylsilyl)pyrrole and 1-methyl-2,5-bis(trimethylsilyl)pyrrole, and (2) with dichlorodimethylsilane gave 2,5-bis(chlorodimethylsilyl)-1-methylpyrrole.