Carbon-carbon bond formation by the use of chloroiodomethane as a C1 unit. III. A convenient synthesis of the Mannich base from enol silyl ether by a combination of …

S Miyano, H Hokari, H Hashimoto

Index: Miyano, Sotaro; Hokari, Hiroshi; Hashimoto, Harukichi Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 2 p. 534 - 539

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Citation Number: 24

Abstract

The Mannich dimethylaminomethylation of carbonyl compounds is conveniently carried out via enol trimethylsilyl ethers by a combination of chloroiodomethane (CH 2 ClI) and N, N, N′, N′-tetramethylmethanediamine (TMMD) in DMSO as the solvent at ambient temperature. The mechanism of the transformation is discussed on the basis of product analysis and 1 H NMR spectral studies. The reagent system CH 2 ClI/TMMD also provides ...