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
Full Text: HTML
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 ...
Related Articles:
[Ghanem, Ashraf; Lacrampe, Fabienne; Aboul-Enein, Hassan Y.; Schurig, Volker Monatshefte fur Chemie, 2005 , vol. 136, # 7 p. 1205 - 1219]
Formal Homo??Nazarov and Other Cyclization Reactions of Activated Cyclopropanes
[De Simone, Filippo; Saget, Tanguy; Benfatti, Fides; Almeida, Sofia; Waser, Jerome Chemistry - A European Journal, 2011 , vol. 17, # 51 p. 14527 - 14538]
S-Ethenylsulfoximine derivatives. Reagents for ethylenation of protic nucleophiles
[Johnson, Carl R.; Lockard, James P.; Kennedy, Eugene R. Journal of Organic Chemistry, 1980 , vol. 45, # 2 p. 264 - 271]
S-Ethenylsulfoximine derivatives. Reagents for ethylenation of protic nucleophiles
[Johnson, Carl R.; Lockard, James P.; Kennedy, Eugene R. Journal of Organic Chemistry, 1980 , vol. 45, # 2 p. 264 - 271]
S-Ethenylsulfoximine derivatives. Reagents for ethylenation of protic nucleophiles
[Johnson, Carl R.; Lockard, James P.; Kennedy, Eugene R. Journal of Organic Chemistry, 1980 , vol. 45, # 2 p. 264 - 271]