REACTION OF POLYMERIZATION-RESISTANT 1,2-DITHIOLANES WITH LITHIATED PICOLINES: SIMPLE RING OPENING AND 1,3-DITHIANE FORMATION

Masato Tazaki Department of Industrial Chemistry, Kumamoto Institute of Technology, Ikeda 4-22-1, Kumamoto, 860, Japan

Shigeyuki Okai Department of Industrial Chemistry, Kumamoto Institute of Technology, Ikeda 4-22-1, Kumamoto, 860, Japan

Toshihiko Hieda Department of Industrial Chemistry, Kumamoto Institute of Technology, Ikeda 4-22-1, Kumamoto, 860, Japan

Shizuo Nagahama Department of Industrial Chemistry, Kumamoto Institute of Technology, Ikeda 4-22-1, Kumamoto, 860, Japan

Makoto Takagi Department of Chemical Science and Technology, Faculty of Engineering, Kyushu University, Hakozaki 6-10-1, Higashi-ku, Fukuoka, 812, Japan

Abstract

Reaction of polymerization resistant 1,2-dithiolanes 1 with excess pyridylmethyllithiums 3 in THF gave the corresponding ring-opened products 2 in good yields, but the by-products 2-pyridyl-1,3-dithianes 5 and 1,3-propanedithiols 6 could not be excluded. Addition of hexamethylphosphoric triamide (HMPT) to the reaction mixture resulted in the selective formation of 5.

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REACTION OF POLYMERIZATION-RESISTANT 1,2-DITHIOLANES WITH LITHIATED PICOLINES: SIMPLE RING OPENING AND 1,3-DITHIANE FORMATION

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REACTION OF POLYMERIZATION-RESISTANT 1,2-DITHIOLANES WITH LITHIATED PICOLINES: SIMPLE RING OPENING AND 1,3-DITHIANE FORMATION

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