The reactions of two σ-anionic compounds (Jackson–Meisenheimer adducts) in liquid ammonia studied by13C nuclear magnetic resonance spectroscopy
- 1 January 1987
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 9,p. 1341-1344
- https://doi.org/10.1039/p29870001341
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.Keywords
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