Preparation and reactivity of acetoacetonitrile dianion
1978; Elsevier BV; Volume: 19; Issue: 44 Linguagem: Inglês
10.1016/s0040-4039(01)95186-x
ISSN1873-3581
AutoresFredric J. Vinick, Yolanda Pan, Heinz W. Gschwend,
Tópico(s)Organic Chemistry Synthesis Methods
ResumoA series of 5-aryl-4-bromo-4-fluoroisoxazolines was synthesized via nitrosation of 2-aryl-1-bromo-1-fluorocyclopropanes with NOBF4. It was shown that the E-isomers of the cyclopropanes react highly regio- and diastereoselectively leading exclusively to the E-isomers of the isoxazolines. The obtained 5-aryl-4-bromo-4-fluoroisoxazolines were transformed selectively into the corresponding 5-aryl-4-fluoro- or 5-aryl-4-bromoisoxazoles in good yields in the reaction with Lewis acids.
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