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Paper | Regular issue | Vol 43, No. 4, 1996, pp.851-859
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7375
Acetal Formation by Metal Ion-mediated Desulfurization-Condensation of Thioketones with Diols and Phenols

Isao Shibuya *, Eisaku Katoh, Yasuo Gama, Akihiro Oishi, Yoichi Taguchi, and Tohru Tsuchiya

*National Institute of Materials and Chemical Research, 1-1 Higashi, Tsukuba, Ibaraki 305, Japan

Abstract

The acetal formation of thioketones with several diols and phenols through metal ion-mediated desulfurization-condensation was investigated. The reactivities of 4,4’-bis(dimethylamino)thiobenzophenone, "thio-Michler’s ketone" (TMK) and xanthene-9-thione (XT) toward α,ω-alkanediols [HO(CH2)nOH, n= 2 ~ 4] in the presence of silver trifluoroacetate and triethylamine were compared. The reaction of TMK with glycerol, trans- and cis-1,2-cyclohexanediols, α,α’-dihydroxy-o-xylene and biphenyl-2,2-diol in the presence of silver salt gave the corresponding acetals in good yields. On the other hand, copper(I) chloride, in place of silver(I) salt, was useful for catechol and pyrogallol to give their acetals, respectively. It was thus found that thioketones are new and versatile acetalizing reagents for diols and phenols.