2815-45-4Relevant academic research and scientific papers
Selective homologation of ketones and aldehydes with diazoalkanes promoted by organoaluminum reagents
Maruoka,Concepcion,Yamamoto
, p. 1283 - 1290 (2007/10/02)
Organoaluminum-promoted single homologation or ring expansion of ketones and aldehydes with diazoalkanes has been described, and among various organoaluminium reagents, exceptionally bulky methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) is found to be highly effective for the selective homologation of various ketones and aldehydes.
Oxidation of Alkenes and Sulphides with a Series of Hydroperoxides having Electron-withdrawing Substituents at the α-Position
Yamamoto, Hiroshi,Miura, Masahiro,Nojima, Masatomo,Kusabayashi, Shigekazu
, p. 173 - 182 (2007/10/02)
The oxidations of alkenes and sulphides with a series of hydroperoxides, α-hydroperoxy-α-methoxyacetophenone (1), α-hydroperoxy-α,α-diphenylacetophenone (2), methyl α-hydroperoxy-α,α-diphenylacetate (3), and α-hydroperoxy-α,α-diphenylacetonitrile (4), were undertaken in a systematic fashion.The data revealed the following. (a) The reactions of electron-rich alkenes (11a and b) with hydroperoxides (1)-(4) are most likely to proceed by a mechanism similar to that with peracids, as do the oxidations of sulphides (5a-e). (b) For the reaction of less reactive alkenes (11f-k) with hydroperoxide (1) in the presence of oxygen, epoxidation by benzoylperoxyl radical contributes to a significantextent.The reaction with hydroperoxide (2) at 60 deg C also seems to proceed by a mechanism involving benzoylperoxyl radical, whereas a molecular epoxidation mechanism is important for the reaction at 30 deg C.Perhaps in accord with this, the reaction of 1,1-disubstituted ethylenes (11c-e) with hydroperoxides (1) and (2) results in the formation of considerable amounts of benzoylated products (13) and (14). (c) For the epoxidation with hydroperoxides (3) and (4), however, a molecular epoxidation process seems to predominate.The exception is the reaction of hydroperoxide (3) with (Z)-2-phenylbut-2-ene and (Z)-stilbene, having very poor reactivity, in which a peroxyl radical, produced by hydrogen abstraction from the hydroperoxide (3), plays an important role in the epoxidation.
NOVEL ONE STEP SYNTHESIS OF EPOXIDES FROM β-HYDROXY-SELENIDES AND SULFIDES
Laboureur, J. L.,Dumont, W.,Krief, A.
, p. 4569 - 4572 (2007/10/02)
Epoxides are stereoselectively prepared in one step from β-hydroxy selenides and β-hydroxy sulfides in a process which involves dichlorocarbene
