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Communication | Regular issue | Vol 31, No. 5, 1990, pp.811-817
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5129
Regioseletivity in the 3,5-Dialkylation of 3,5-Dimethyl-4-(4-methylcyclohexen-1-yl)isoxazole

Cecilia Polo, Vicente Ramos, Tomás Torroba,* Ricardo Bossio, Stefano Marcaccini, and Roberto Pepino

*Departamento de Química Orgánica, Facultad de Veterinaria, Universidad de Extremadura, 10071 Cáceres, Spain


3,5-Dimethyl-4-(4-methylcyclohexen-1-yl)isoxazole reacts with β-methallyl chloride and either lithium isopropylcyclohexylamide or n-butyhyllithium in THF to afford the three alkylation products II, III, IV, in yields controlled by the ratio of isoxazole:base:halide.