Tetrahedron

3-Halomethylated cyclic nitronates: synthesis and nucleophilic substitution

…, MI Struchkova, YA Khomutova, AA Korlyukov, SL Ioffe…

Index: Mikhaylov, Andrey A.; Dilman, Alexander D.; Struchkova, Marina I.; Khomutova, Yulia A.; Korlyukov, Alexander A.; Ioffe, Sema L.; Tartakovsky, Vladimir A. Tetrahedron, 2011 , vol. 67, # 25 p. 4584 - 4594

Full Text: HTML

Citation Number: 8

Abstract

Abstract A method for the introduction of a halogen atom into the methyl group attached to the C-3 atom of five-and six-membered cyclic nitronates (isoxazoline N-oxides and oxazine N-oxides, respectively) has been studied. The process involves silylation of starting 3-methyl- substituted cyclic nitronates followed by halogenation of the resulting N-(silyloxy) enamines. While five-and six-membered cyclic enamines behave similarly toward elemental bromine ...