[14180-63-3] · C6H10OS · Diallyl Sulfoxide · (MW 130.20)
(source of thioacrolein in solution1)
Physical Data: colorless oil solidifying at 5 °C.
Solubility: sol most organic solvents.
Preparative Method: conveniently prepared in 91% yield from commercially available diallyl sulfide by oxidation with 30% H2O2 in acetone at rt followed by recrystallization at -20 °C from pentane/ether.1
When an excess of diallyl sulfoxide (or a homolog such as bis(2-methyl-2-propenyl) sulfoxide) is heated with dienophiles, thioacrolein Diels-Alder adducts, 3,4-dihydro-2H-thiopyrans, are formed in good to excellent yield (eq 1 and Table 1).1
State University of New York at Albany, NY, USA