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Paper | Special issue | Vol 50, No. 2, 1999, pp.681-692
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)23
Regiocontrolled Carbonylsulfanylations at ortho-Position of Phenols and at α-Position of Ketones Using Chlorocarbonylsulfenyl Chloride

Yoshihiro Yoshida, Masahiro Ogura, and Yoo Tanabe*

*School of Science, Kwansei Gakuin University, 1-1-155 Uegahara, Nishinomiya 662-8501, Japan


Bu3N/AlCl3-promoted [3+2] cyclocondensation between phenols and chlorocarbonylsufenyl chloride (CCSC ; 3) gave 1,3-benzoxathiol-2-ones (2), wherein the acylation of phenols with CCSC (3) and the intramolecular and regioselective ortho-sulfenylation successively proceeded in a one-pot manner. 2-Sulfanylphenols (1) were produced from 2 by mild hydrolysis using NaOH. An analogous Bu3N-promoted [3+2] cyclocondensation between ketones and 3 gave 1,3-oxathioles (7), wherein the α-CH2- position of the ketones was regioselectively sulfenylated.