REACTIONS OF 4-PENTENOIC ACID WITH SULFENYL CATIONS GENERATED ELECTROCHEMICALLY FROM BISQUINOLINYL AND BISPYRIDINYL DISULFIDES

摘要

Lactonization of 4-pentenoic acid to 5-(azinylthio)methyloxolan-2-ones (8) was performed by addition of electrochemically generated azinylsulfenyl cations starting from the respective 3,3'-bis(pyridinyl or quinolinyl) disulfides (2) or (5) and 4,4'-bis(7-chloroquinolinyl or 3-methylthioquinolinyl) disulfides (6b),(6c) and using a bromide ion as a redox catalyst.Sulfenyl cations generated in the same manner from 2,2'-bispyridinyl and 2,2'-bisquinolinyl disulfides (1) or (4) reacted with 4-pentenoic acid to form thiazolo[3,2-a]pyridinio- or quinoliniopropanoate (9a) or (9b).In the case of 8,8'-bisquinolinyl disulfide (7),oxolan-2-one (8e) was accompanied by 2,3-dihydro-l,4-thiazinequinolinio derivative (10).4,4'-Bis(pyridinyl nor quinolinyl) disulfides (3) and (6a) did not give such products.