Diallyl Sulfoxide

[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

In Situ Generation and Trapping of Thioacrolein: Synthesis of 3,4-Dihydro-2H-thiopyrans.

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

1. Block, E.; Zhao, S.-H. TL 1990, 31, 5003.

Eric Block

State University of New York at Albany, NY, USA

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