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Communication | Regular issue | Vol 23, No. 8, 1985, pp.1873-1879
Published online, 1st January, 1970
DOI: 10.3987/R-1985-08-1873
Carbon-carbon Bond Forming Reaction of Bis(chloromethyl)sulfone with Carbonyl Compounds: General Route to Aromatic 2-Chlorovinyl Compounds and α-Hydroxyaldehydes

Enkou Nagashima, Kunio Suzuki, Motoaki Ishikawa, and Minoru Sekiya*

*Shizuoka College of Pharmacy, 2-2-1, Oshika, Shizuoka-shi, 442 Shizuoka, Japan

Abstract

Bis(chloromethyl)sulfone (1) has been proved to be a useful reagent for the synthesis of aromatic 2-chlorovinyl compounds (4) from aromatic aldehydes and of α-hydroxyaldehydes (5) from aliphatic carbonyl compounds with one carbon prolongation. The sec-butyllithium-aided reaction of 1 with aromatic aldehydes gives 1,3-oxathiolane-3,3-dioxides (2) which are converted to 4 in good yields by thermolysis. On the other hand, the sodium hydride-aided reaction of 1 with aliphatic carbonyl compounds is favorable to the formation of chloromethylsulfonyloxiranes (3). Titanium tetrachloride has been found to be an efficient reagent for hydrolysis of 3 to 5.