Diethyl Ether → 2,2-Dinitro-3-phenylbutane

Participants

Reaction Conditions

Reaction Steps

To a solution of 4.03 g (0.025 mol) of 2-nitro-1-phenyl-1-propene dissolved in 30 ml of dry THF (cooled to -40° C. with an acetronitrile-dry ice bath) and under a positive nitrogen atmosphere was added with stirring 22 ml (0.05 mol) of a 5% ether solution of methyllithium. The resulting solution was stirred for 1 h at -40° C. followed by the addition of 4.9 g (0.025 mol) of tetranitromethane. The solution was then allowed to warm to room temperature and stirred an additional hour. The resulting product was isolated and purified as described in Example 1 above, yielding 3.4 g (60% yield) of an analytically pure white crystalline product, mp 76°-78° C. A similar procedure was used for the preparation of derivatives wherein R3 (see structure above or scheme) was CH3 (CH2)3 and R2 was H and wherein R3 was CH3 and R2 was CH3 (see scheme).

Provenance & Evidence