Fluorosilyl(pyrrolyl)silylamines as precursors for intra- and intermolecularly stabilized iminosilanes
作者:A. Frenzel、R. Herbst-Irmer、U. Klingebiel、S. Rudolph
DOI:10.1016/s0022-328x(96)06429-7
日期:1996.11
Three indolyl- and pyrrolylsilylamines 1-3 were prepared from lithiated heterocyclics and fluorosilylamines. Further reaction with di-tert-butyldifluorosilane led to the fluorosilylpyrrolylsilylamines 4 and 5. The fluorosilylpyrrolylsilylamine 6 was prepared by reaction of bis(fluorodiisopropylsilyl)amine and lithium pyrrolide. Lithiiation with n-butyllithium of 4-6 solved in THF gave the iminosilane-LiF adducts 7-9; in contrast, lithiation of 5 in n-hexane led to the lithium fluorosilylamid 10. Heating of the iminosilane-LiF adduct 7 gave the bicyclic system 11, an intramolecularly stabilized iminosilane. Addition of chlorotrimethylsilane to 9 led to fluorine-chlorine exchange and elimination of lithium chloride. The product is the intermolecular stabilization of the intermediate iminosilane as a four-membered ring 12. The X-ray structures of 1, 11 and 12 have been determined.