Methyltrioxorhenium-Catalyzed Oxidation of Secondary and Primary Amines with Hydrogen Peroxide
作者:Shigekazu Yamazaki
DOI:10.1246/bcsj.70.877
日期:1997.4
The methyltrioxorhenium-catalyzed oxidation of secondaryamines and primaryamines with hydrogen peroxide has been carried out. The oxidation of secondaryamines afforded nitrones in good-to-excellent yield. Benzylamines were selectively oxidized to oximes, while general primary alkylamines possessing the α-C–H bond gave mixtures of oximes, nitroso dimers, and azoxy compounds.
The present invention relates to a process for preparing C
4
-C
15
lactams, in which a C
1
-C
10
-alkyl nitrite is reacted with a C
4
-C
15
-cycloalkane and is illuminated with a light-emitting diode during the reaction. This forms a C
4
-C
15
-cyclohexanone oxime which is then converted further to a C
4
-C
15
lactam; the C
1
-C
10
alcohol formed is recycled into the preparation of the C
1
-C
10
-alkyl nitrite.
The Reaction of Nitrosoalkane Dimers with Acid Halides
作者:Max A. Ribi、Emil H. White
DOI:10.1002/hlca.19750580116
日期:——
Nitrosoalkane dimers react with acid halides to yield α-halogeno-azoxy compounds with the substituent α to the oxygen-bearing nitrogen. In the presence of silver carbonate, the corresponding α-acyloxy-azoxy compounds are formed.
Oxidation of primary aliphatic amines with sodium perborate
作者:Walter W Zajac、Michael G Darcy、Amador P Subong、John H Buzby
DOI:10.1016/s0040-4039(01)89003-1
日期:1989.1
A biphasic system of ethyl acetate and water containing sodium perborate, sodium bicarbonate and N,N,N′N′-tetraacetylethylenediamine oxidizes primaryaliphaticamines to aliphatic C-nitroso compounds in good to excellent yields.
Several primary amines 2 have been oxidized with dimethyldioxirane (1) under a variety of conditions. Mixtures of dimeric nitrosoalkanes 4 and oximes 5 were typically obtained with solutions of the oxidant in excess. In several instances, nitrones 12 were found as byproducts in these reactions. In situ oxidations using oxone in buffered aqueous acetone solution also gave nitrosoalkanes 4 and oximes 3 as important products; in addition, oxaziridines 11 were obtained in significant amounts in biphasic procedures containing methylene chloride. The corresponding nitroalkanes 3 were not formed in major amounts in either oxidation procedure, unless large excesses of oxidant were used. These results are discussed in terms of the several competing processes which occur under the different reaction conditions.