TOTAL STEREOSPECIFICITY IN FREE RADICAL INTRAMOLECULAR ADDITION: CYCLISATION OF CIS AND TRANS 1-METHYL 4-HEXENYL N-CHLOROAMINES BY MEANS OF METALLIC SALTS
Extremely high stereospecificity (up to 100percent diastereoisomeric purity) can be obtained for the metallic salts induced radical cyclisation of the cis and trans 1-methyl 4-hexenyl N-chloroamines.A possible mechanism for the highly effective trans-addition using metal-complexed aminyl radical is proposed.
Bougeois, Jean-Luc,Stella, Lucien,Surzur, Jean-Marie
A practical, general and efficient protocol for the catalytic epoxidation of alkenes has been developed.The in situ generation of reactive dioxiranes capable of epoxidizing a variety of alkenes under biphasic conditions has been accomplished using phase transfer catalysts bearing a carbonyl group.Optimal epoxidation conditions employ 10 mol percent of 1-dodecyl-1-methyl-4-oxopiperidinium triflate (8d(+)OTf(-)) in a CH2Cl2/pH 7.5-8.0 biphase using potassium monoperoxosulfate (Oxone) as the oxidant.Optimization of the conditions identified (1) slow addition rate, (2) pH 7.5-8.0, (3) N-dodecyl chain, and (4) the triflate salt as key experimental and structural variables.A selection of nine olefins was successfully oxidized to the corresponding epoxides in 83-96percent yield.
Denmark, Scott E.,Forbes, David C.,Hays, David S.,DePue, Jeffrey S.,Wilde, Richard G.
p. 1391 - 1407
(2007/10/02)
REACTIONS OF ORGANIC HALIDES WITH OLEFINS UNDER Ni0-CATALYSIS. FORMAL ADDITION OF HYDROCARBONS TO CC-DOUBLE BONDS
The reaction of various types of organic halides with electron deficient olefins under the influence of NiCl2 x 6 H2O in the presence of zinc and pyridine leads to formal addition products of hydrocarbons to CC-double bonds in good yield.
Sustmann, Reiner,Hopp, Peter,Holl, Peter
p. 689 - 692
(2007/10/02)
Pheromones, XXXII. - Synthons for the preparation of bisolefinic lepidoptera pheromones
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Bestmann,Koschatzky,Schaetzke,et al.
p. 1705 - 1720
(2007/10/02)
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