- Preparation of alcohols from sulfones and trialkylboranes
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The reaction of sulfone anions with trialkylboranes followed by thermal isomerization of the obtained boron compounds in the presence of excess borane-methyl sulfide complex and by alkaline hydroperoxide oxidation yields primary alcohols.
- Billaud, Célia,Goddard, Jean-Philippe,Le Gall, Thierry,Mioskowski, Charles
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p. 4451 - 4454
(2007/10/03)
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- Olefin Synthesis by Vanadium(V)-Induced Oxidative Decarboxylation-Deoxygenation of 3-Hydroxy Carboxylic Acids
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Oxidative decarboxylation of 3-hydroxy carboxylic acids can be effected with various V(V) complexes.This process likely yields an intermediate 1,4-metalla diradical. β-elimination from this intermediate gives olefin and regenerates V(V), likely as VO2Cl.Thus, although the overall process involves no net change in oxidation state for vanadium, the decarboxylation process is oxidatively induced.Intramolecular trapping of the intermediate yields glycolate and then C-C cleavage products, and skeletal rearrangement gives ketonic products.Qualitatively, rates for oxidative decarboxylation of the acids and the stereospecificity of formation of olefinic products depend on the electron-withdrawing ability of groups attached to vanadium.Methodology is described for the preparation of tri- and tetrasubstituted olefins in high yield from appropriate 3-hydroxy carboxylic acid precursors.
- Meier, Ingrid K.,Schwartz, Jeffrey
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p. 5619 - 5624
(2007/10/02)
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- DENITROHYDROGENATION OF ALIPHATIC NITRO COMPOUNDS AND A NEW USE OF ALIPHATIC NITRO COMPOUNDS AS RADICAL PRECURSORS
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Aliphatic nitro groups are replaced by hydrogen on treatment with tributyltin hydride which proceeds via free radical chain processes.As the nitro group is selectively denitrated and other reducible groups are not affected with tributyltin hydride, this reaction can be used as a method for removing the nitro group from polyfunctional compounds.The radical intermediates generated via denitration can be also used for the carbon-carbon bond forming reactions.
- Ono, Noboru,Miyake, Hideyoshi,Kamimura, Akio,Hamamoto, Isami,Tamura, Rui,Kaji, Aritsune
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p. 4013 - 4024
(2007/10/02)
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- REACTION OF 1,3-ALKADIENES WITH ARENEDIAZONIUM CHLORIDES IN THE PRESENCE OF IRON(II) CHLORIDE
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The reaction of arenediazonium chlorides with 1,3-alkadienes in the presence of iron(II) chloride was investigated.It was established that the reaction takes place with the formation of products from chloroarylation of the dienes, telomerization, and additive dimerization.A method is proposed for the synthesis of diaryloctatetraenes containing substituents in the aromatic rings and in the aliphatic chain.
- Ganushchak, N. I.,Obushak, N. D.,Polishchuk, O. P.
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p. 633 - 639
(2007/10/02)
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