Tetrahedron

β-silylation of N-alkylpyrroles, experimental support of theoretical calculations

MW Majchrzak, G Simchen

Index: Majchrzak, Michal W.; Simchen, Gerhard Tetrahedron, 1986 , vol. 42, # 5 p. 1299 - 1304

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Citation Number: 24

Abstract

The β-substitution of N-alkylpyrroles which is “unusual” but predicted by theoretical calculations, was supported by the 1H-NMR and GC/MS analysis of the reaction products of 1-methylpyrrole-2, 5-d2 (1a) with trimethylsilyl trifluoromethane-sulfonate (2) in triethylamine (3). Thus, 1a gives with 2 in 3 predominantly the β-isomer 5b (two deuteriums) and small amounts of the α-isomer 4a (one deuterium). The formation of these products of such a ...