Substituted isoxazolidines formed by 1,3-dipolar cycloaddition of nitrones to alkenes undergo ring-opening elimination to α,β-enones when treated with trimethyl phosphate. The reaction involves initial alkylation giving the isoxazolidinium intermediate which collapses to the α,β-enone by a Hofmann-like elimination having an orientation controlled by electronic factors, the first step being rate-determining.
N,O-heterocyclics13;-14conversion of isoxazolidines into α,β enones / Liguori, A; Sindona, Giovanni; Uccella, N.. - In: TETRAHEDRON. - ISSN 0040-4020. - 40:10(1984), pp. 1901-1906.
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Titolo: | N,O-heterocyclics13;-14conversion of isoxazolidines into α,β enones |
Autori: | |
Data di pubblicazione: | 1984 |
Rivista: | |
Citazione: | N,O-heterocyclics13;-14conversion of isoxazolidines into α,β enones / Liguori, A; Sindona, Giovanni; Uccella, N.. - In: TETRAHEDRON. - ISSN 0040-4020. - 40:10(1984), pp. 1901-1906. |
Handle: | http://hdl.handle.net/20.500.11770/135234 |
Appare nelle tipologie: | 1.1 Articolo in rivista |