Tetrahedron

Competition between vinylic substitution and conjugate addition in the reactions of vinyl selenoxides and vinyl selenones with nucleophiles in DMF

M Tiecco, D Chianelli, L Testaferri, M Tingoli, D Bartoli

Index: Tiecco, Marcello; Chianelli, Donatella; Testaferri, Lorenzo; Tingoli, Marco; Bartoli, Donatella Tetrahedron, 1986 , vol. 42, # 17 p. 4889 - 4896

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Citation Number: 29

Abstract

Vinyl selenoxides and vinyl selenones present a different reactivity towards thiolate or alkoxide anions in DMF. In the case of selenoxides the addition of the nucleophiles regioselectively occurs at the α-carbon leading to the formation of the vinylic substitution products with complete retention of configuration. These reactions occur under very mild conditions indicating that the seleninyl group markedly enhances nucleophilic vinylic ...