18684-89-4Relevant academic research and scientific papers
CARBON-CARBON BOND FORMING REACTION OF BIS(CHLOROMETHYL)SULFONE WITH CARBONYL COMPOUNDS: GENERAL ROUTE TO AROMATIC 2-CHLOROVINYL COMPOUNDS AND α-HYDROXYALDEHYDES
Nagashima, Enkou,Suzuki, Kunio,Ishikawa, Motoaki,Sekiya, Minoru
, p. 1873 - 1879 (2007/10/02)
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.
