1992
DOI: 10.1039/p19920003161
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A novel, chemoselective, ‘one-pot’ procedure for the simultaneous denitration–deoxygenation of 2-nitroketones by TsNHNH2–NaBH4

Abstract: Chemoselective conversion of both the carbonyl group and the carbon bearing the nitro group, of 2-nitro ketones, into two methylenes is performed in one pot, under mild conditions.

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Cited by 12 publications
(3 citation statements)
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“…When α‐nitroketones were treated in a one‐pot procedure sequentially with tosylhydrazine and sodium borohydride, a remarkable reduction to alkanes 276 – 281 was achieved (Scheme 14). [238] Apart from the protodenitration, smooth direct deoxygenation occurred at 80 °C.…”
Section: Protodenitration Employing Complex Metal Hydridesmentioning
confidence: 99%
“…When α‐nitroketones were treated in a one‐pot procedure sequentially with tosylhydrazine and sodium borohydride, a remarkable reduction to alkanes 276 – 281 was achieved (Scheme 14). [238] Apart from the protodenitration, smooth direct deoxygenation occurred at 80 °C.…”
Section: Protodenitration Employing Complex Metal Hydridesmentioning
confidence: 99%
“…In 1991, Ballini 84 published the synthesis of both (6Z)-henicos-6-en-11-one (6.87), the Douglas fir tussock moth (Orgyia pseudotsugata) sex pheromone and (6Z)-non-6-en-2-one (6.88), an intermediate for the synthesis of brevicomin, the sex pheromone of the Western pine beetle (Dentroctonus brevicomis). The functionalized nitroalkanes explored for this purpose have been prepared from commercial alkenols by conversion into the corresponding bromides and substitution with sodium nitrite in DMF.…”
Section: Reviewmentioning
confidence: 99%
“…The sex pheromone of the Douglas-Fir Tussock moth 22 (Scheme 10) has been prepared by the help of the nitroaldolic strategy [48]. The Henry reaction (19 + 20) was mediated by neat Amberlyst A-21.…”
Section: Natural Products Synthesismentioning
confidence: 99%