93274-30-7Relevant articles and documents
N,O-HETEROCYCLICS-14 CONVERSION OF ISOXAZOLIDINES INTO α,β-ENONES
Liguori, Angelo,Sindona, Giovanni,Uccela, Nicola
, p. 1901 - 1906 (1984)
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.