Tetrahedron

Formation and reactivity of the addition products of alkoxides and thiolate anions to vinyl selenones

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

Index: Tiecco, Marcello; Chianelli, Donatella; Tingoli, Marco; Testaferri, Lorenzo; Bartoli, Donatella Tetrahedron, 1986 , vol. 42, # 17 p. 4897 - 4906

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Citation Number: 18

Abstract

Vinyl selenones react with sodium methanethiolate in methanol to give the product of conjugate addition and subsequent displacement of the selenonyl group. On the contrary, the same reaction carried out with alkoxide anions affords the conjugate addition products in excellent yields. These β-alkoxy alkyl phenyl selenones are stable compounds which can react in several ways with loss of the selenonyl group. Their reactions with MeONa or ...

~47%

~30%

~47%

~5%

~42%

~42%

~45%

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