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Paper | Special issue | Vol 74, No. 1, 2007, pp.791-802
Published online, 9th November, 2007
DOI: 10.3987/COM-07-S(W)65
Reaction of 2-Alkylthiopyridinium Salts with Active Methylene Compounds

Masato Hoshino, Tsuyoshi Taguchi, Hiroto Nakano, Hiroshi Tomisawa, Hisao Matsuzaki, and Reiko Fujita*

*Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Abstract

Reactions between active methylene compounds and 2-alkyllthio-1-alkylpyridinium iodides in the presence of sodium hydride, were found to occur at the 2 or 4-position. In contrast, 2-chloro-1-methylpyridinium iodide reacted at the 2-position, whereas 6-chloro-2-methylthiopyridinium iodide reacted at the 6-position to yield only one product. Chemoselectivity of the pyridinium salt was calculated using molecular orbital (MO) calculations.