The reactions of two σ-anionic compounds (Jackson–Meisenheimer adducts) in liquid ammonia studied by 13C nuclear magnetic resonance spectroscopy

Abstract

The reactions of the Jackson–Meisenheimer adducts derived from: (a) methoxide ion and 1,3,5-trinitrobenzene; (b) acetone carbanion and 1,3,5-trinitrobenzene, in liquid ammonia solution have been studied by ¹³C n.m.r. With the adduct (a) the methoxy group is labile as expected, whereas with (b) the C–C bond on the ring sp³ carbon atom remains unbroken, but cyclisation through the γ-carbon of the acetonyl group occurs to form a bicyclo-derivative.