3378-45-8

Usage

InChI:InChI=1/C12H22N2O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h11-12H,1-10H2

Upstream product

• 110-82-7 cyclohexane 
• 2211-64-5 N-cyclohexyl-hydroxylamine 
• 1122-60-7 1-nitrocyclohexane 
• 108-91-8 cyclohexylamine 
• 67-64-1 acetone 
• 75-52-5 nitromethane 

Downstream Products

• 100-64-1 cyclohexanone-oxime 
• 54978-08-4 N-(1-Chloro-cyclohexyl)-N'-cyclohexyl-diazene N-oxide 
• 1781-74-4 (Z)-Dicyclohexyldiazen-1-oxid 
• 57497-35-5 (Z)-Methylcyclohexyldiazen-1-oxid 
• 35214-90-5 (Z)-Cyclohexylmethyldiazen-1-oxid 

Relevant academic research and scientific papers

Photochemical Flow Oximation of Alkanes

The nitrosation of several alkanes using tert-butyl nitrite has been performed in flow showing a remarkable reduction in the reaction time compared with batch processing. Due to the necessity for large excesses of the alkane component a continuous recycling process was devised for the preparation of larger quantities of material.

METHOD FOR PRODUCING C4-C15 LACTAMS

The present invention relates to a process for preparing C4-C15 lactams, in which a C1-C10-alkyl nitrite is reacted with a C4-C15-cycloalkane and is illuminated with a light-emitting diode during the reaction. This forms a C4-C15-cyclohexanone oxime which is then converted further to a C4-C15 lactam; the C1-C10 alcohol formed is recycled into the preparation of the C1-C10-alkyl nitrite.

Methyltrioxorhenium-Catalyzed Oxidation of Secondary and Primary Amines with Hydrogen Peroxide

The methyltrioxorhenium-catalyzed oxidation of secondary amines and primary amines with hydrogen peroxide has been carried out. The oxidation of secondary amines 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.

Dimethyldioxirane Oxidation of Primary Amines

Several primary amines 2 have been oxidized with dimethyldioxirane (1) nder 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 solutions 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 5 were not formed in major amounts in either oxidation procedures, unless large excesses of oxidant were used.These results are discussed in terms of several competing processes which occur under the different reaction conditions.

OXIDATION OF PRIMARY ALIPHATIC AMINES WITH SODIUM PERBORATE

A biphasic system of ethyl acetate and water containing sodium perborate, sodium bicarbonate and N,N,N',N'-tetraacetylethylenediamine oxidizes primary aliphatic amines to aliphatic C-nitroso compounds in good to excellent yields.

Oxidation of Primary Aliphatic Amines to C-Nitroso Dimers

A biphasic system of ethyl acetate or dichloromethane and water containing sodium percarbonate (Na2CO3*3/2H2O2), sodium hydrogen carbonate and N,N,N',N'-tetraacetylethylenediamine oxidizes primary aliphatic amines to aliphatic C-nitroso dimers in most cases in good to excellent yields.

REDUCTION OF AROMATIC AND ALIPHATIC NITRO COMPOUNDS BY SODIUM HYDROGEN TELLURIDE

Various nitro compounds were effectively reduced by sodium hydrogen telluride in good yields.Thus, reductive conversion of unhindered nitrobenzenes to azoxybenzenes, sterically hindered nitrobenzenes to anilines, nitroalkanes to dimer of nitrosoalkanes, and vicinal-dinitroalkane to olefin was achieved.

Photochemical Studies of Nitromethane in Solution. II. Nitromethane in Cyclohexane

Continuous photolysis of nitromethane in solution of cyclohexane at 254 nm and λ >290 nm at 298+/-1 K is described.Significant differences in the progress of the reaction depending on the wavelenghts applied have been observed.Irradiation of nitromethane at 254 nm has led to the photostationary state with trans-nitrosocyclohexane dimer formation as a major reaction product.This dimer was not formed when the system was irradiated with wavelenghts: λ >290 nm and λ = 313 nm.Quantum yields of photoproducts formation have been measured at 254 nm and 313 nm.Possible mechanisms of their formation are discussed.The secondary photolysis of nitrosodimer at 313 nm is probably responsible for the differences in the photochemistry of nitromethane in cyclohexane and excited at different wavelengths.