Uses
1,1-Bis(phenylsulfonyl)ethylene was used in the preparation of α,α-disubstituted alpha-amino acid derivatives.
Application
1,1-Bis(phenylsulfonyl)ethylene (1,1-BPSE) is a powerful Michael acceptor and dienophile; reagent for two-carbon homologation of ketones; synthetic equivalent of ethylene in Diels-Alder reactions and of ethylene 1,2-dipole in cycloadditions[1].
Preparation
1,1-Bis(phenylsulfonyl)ethylene can be prepared via careful oxidation of the corresponding ketene
dithioacetal or via Mannich condensation of bis(phenylsulfonyl)methane with paraformaldehyde and a
secondary amine followed by elimination with acids[2].
storage
1,1-Bis(phenylsulfonyl)ethylene keep dry and refrigerated; potential alkylating agent; use in a fume
hood.
References
1. (a) Neplyuev, V. M.; Bazarova, I. M.; Lozinskii, M. O. RCR 1986, 55, 883. (b) De Lucchi, O.; Pasquato, L. T 1988,
44, 6755. (c) Simpkins, N. S. In Sulphones in Organic Synthesis; Pergamon: Oxford, 1993.
2. (a) Carpino, L. A. JOC 1973, 38, 2600. (b) Stetter, H.; Steinbeck, K. LA 1974, 1315.
