Tetrahedron

Alkenyl nitrones cyclizations induced by phenylselenenyl bromide. A convenient synthetic route to 1, 2-oxazines

M Tiecco, L Testaferri, L Bagnoli

Index: Tiecco, Marcello; Testaferri, Lorenzo; Bagnoli, Luana Tetrahedron, 1996 , vol. 52, # 19 p. 6811 - 6822

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Citation Number: 12

Abstract

Alkenyl nitrones reacted with phenyselenenyl bromide to afford ring closure reaction products deriving by the intramolecular capture of the seleniranium intermediates by the oxygen atom. Owing to the relative positions of the oxygen atom and of the carbon-carbon double bond in the nitrones employed, six-membered cyclic iminium salts were thus formed. These have ben directly treated with nucleophilic reagents and afforded 1, 2-oxazine ...