LIGAND EXCHANGE AND LIGAND COUPLING VIA THE σ-SULFURANE INTERMEDIATE IN THE REACTION OF ALKYL 2-PYRIDYL SULFOXIDE WITH GRIGNARD …

S Oae, T Kawai, N Furukawa

Index: Oae, Shigeru; Kawai, Tsutomu; Furukawa, Naomichi Phosphorus and Sulfur and the Related Elements, 1987 , vol. 34, p. 123 - 132

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Citation Number: 29

Abstract

Abstract The reaction between methyl 2-pyridyl sulfoxide (1) with Grignard reagents afforded 2, 2′-bipyridine (2) in moderate yield. The reaction is considered to involve initial ligand exchange to generate 2-pyridylmagnesium halide which in the subsequent step attacks the original sulfoxide to form the σ-sulfurane that undergoes ligand coupling to afford 2. The reaction of t-butyl 2-pyridyl sulfoxide (3) with C6H5MgBr, however, gave only 2- ...

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