The crystal structure of the σ-complex of 4,6-dinitrobenzofuroxan and potassium 2-nitropropenide
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 3,p. 361-366
- https://doi.org/10.1039/p29920000361
Abstract
A crystalline σ-complex (4d) of 4,6-dinitrobenzofuroxan and potassium 2-nitropropenide has been prepared and characterized by single-crystal X-ray analysis. There are two K+ and two independent anionic 2-nitropropane DNBF moieties per asymmetric unit. A cis-configuration of the hydrogen and NO2 substituents is observed. This structure determination suggests a syn-elimination process for the loss of nitrous acid from 4d which readily occurs in Me2SO solution to give the carbanion (6d) of 4,6-dinitro-7-methylbenzofuroxan.Keywords
This publication has 33 references indexed in Scilit:
- Unusual structure in Meisenheimer complex formation from the highly electrophilic 4,6-dinitrobenzofuroxanThe Journal of Organic Chemistry, 1988
- Ambident nucleophilic reactivity in .sigma.-complex formations. 6. Reactivity-selectivity relationships in reactions of ambident nucleophiles with the superelectrophiles 4,6-dinibrobenzofuroxan and 4,6-dinitro-2-(2,4,6-trinitrophenyl) benzotriazole 1-oxideThe Journal of Organic Chemistry, 1987
- Nonconventional electrophilic heteroaromatic substitutions: ring vs. side-chain reactivity of 2,5-dimethyl five-membered ring heterocycles toward electron-deficient aromaticsThe Journal of Organic Chemistry, 1984
- Ambident aniline reactivity in Meisenheimer complex formationJournal of the American Chemical Society, 1983
- Π-Excessive five-membered ring heteroaromatics acting as carbon nucleophiles towards an electrophilic aromatic.Tetrahedron Letters, 1983
- Direct (uncatalysed) formation of Meisenheimer complexes from primary, secondary and tertiary arylaminesTetrahedron Letters, 1983
- Explosive Meisenheimer complexes formed by addition of nucleophilic reagents to 4,6-dinitrobenzofurazan 1-oxideAustralian Journal of Chemistry, 1983
- Rate and equilibrium studies in Jackson-Meisenheimer complexesChemical Reviews, 1982
- Reactivity of carbon acids toward 4,6-dinitrobenzofuroxan. Studies of keto-enol equilibriums and diastereoisomerism in carbon-bonded anionic .sigma. complexesThe Journal of Organic Chemistry, 1981
- Meisenheimer complexes: a kinetic study of water and hydroxide ion attacks on 4,6-dinitrobenzofuroxan in aqueous solutionJournal of the American Chemical Society, 1976