112175-86-7Relevant articles and documents
N,O-Heterocycles. Part 18. Regiochemistry and Site Selectivity of N-Alkylhydroxylamine Addition to 2,3-Diphenylcyclopropenone
Liguori, Angelo,Sindona, Giovanni,Uccella, Nicola
, p. 961 - 967 (2007/10/02)
This paper evaluates the reactivity of 2,3-diphenylcyclopropenone towards N-alkylhydroxylamines and 2,2-dimethylnitrosoethane (4).CPO preferentially affords 2-methyl-4,5-diphenylisoxazol-3(2H)-one when it is treated with N-methylhydroxylamine, while treatment with higher homologues gives rise to acyclic products. 3,4-Diphenyl-2-t-butylisoxazol-5(2H)-one is formed when substrate (1) reacts with (4).The formation of the products is strongly affected by the oxidizing power of the α- nucleophiles which drive the population of the observed reaction channels from the 1,2 or 1,4 adducts initially formed.A general mechanism is proposed whereby isoxazolones are formed from CPO and both nitroso compounds and hydroxylamine.