Copper-catalyzed aerobic aliphatic C–H oxygenation with hydroperoxides
作者:Pei Chui Too、Ya Lin Tnay、Shunsuke Chiba
DOI:10.3762/bjoc.9.138
日期:——
We report herein Cu-catalyzed aerobicoxygenation of aliphatic C-H bonds with hydroperoxides, which proceeds by 1,5-H radical shift of putative oxygen-centered radicals (O-radicals) derived from hydroperoxides followed by trapping of the resulting carbon-centered radicals with molecular oxygen.
Cyclization towards Carbon-Carbon Double Bond. III. A New Synthesis of 1-Pyrroline Derivatives and a Synthesis of 1, 2-Dialkyl-3-diphenyl-methlenepyrrolidine Alkyl Halide, an Anti-acetylcholine Substance
2-Subsituted 3-diphenylmethylene-1-pyrrolines (III) were synthesized in one step by the reaction of 1, 1-diphenyl-1, 4-butanediol (VII), 2, 2-diphenyltetrahydrofuran (VI), or 4-bromo-1, 1-diphenyl-1-butene (V) with nitrile-stannic chloride complex. 2, 5-Dimethyl (XI) and 2, 5, 5-trimethyl-3-diphenylmethylene-1-pyrroline (XII) were obtained respectively from 1, 1-diphenyl-1, 4-pentanediol (IX) and 1, 1-diphenyl-4-methyl-1, 4-pentanediol (X). The fact that 2-methyl-3-isopropylidene-1-pyrroline (XIV) was obtained from 2-methyl-2, 5-pentanediol (XIII) and 2, 2-dimethyltetrahydrofuran (XV) by the same reaction was of interest in contrast with preparation of 1-pyrrolines (II) by the Ritter reaction. Reduction of the methiodide of III with sodium borohydride gave 1-methyl-2-alkyl-3-diphenylmethylenepyrrolidine. The methiodide of the 2-methyl compound (XVIc) was found to have a comparatively strong anti-acetylcholine activity.
γ-Butyltelluro-2-butanol: a route to reactive 1,4-dianion intermediates
作者:Jefferson L. Princival、Simone M.G. de Barros、João V. Comasseto、Alcindo A. Dos Santos
DOI:10.1016/j.tetlet.2005.05.002
日期:2005.6
gamma-Butyltelluro-2-butanol was reacted with 2 equiv of n-butyllithium. Both tellurium/lithium exchange and the proton abstraction reactions took place in a single step and the lithium dianion intermediate efficiently reacted with aldehydes and ketones, producing the corresponding diols. (c) 2005 Elsevier Ltd. All rights reserved.