61713-85-7

Upstream product

• 15500-74-0 4-chlorobenzonitrile N-oxide 
• 69305-79-9 N,N-diethylamino benzamidoxime 
• 74903-80-3 (Z)-N-hydroxy-4-chloro-benzenecarboximidoyl chloride 
• 188118-38-9 4-Chloro-N,N-diethyl-N'-hydroxy-benzamidine 
• 28123-63-9 4-chlorobenzohydroximoyl chloride 

Downstream Products

• 623-03-0 4-Cyanochlorobenzene 
• 790-41-0 4-chlorobenzoic anhydride 
• 158042-17-2 3,5-bis(4-chlorophenyl)-1,2,4-oxadiazole 

Relevant academic research and scientific papers

Photogeneration and reactivity of acyl nitroso compounds

Acyl nitroso compounds have been generated by photolysis of several different classes of precursors including 9,10-dimethylanthracene adducts, nitrodiazo compounds, and 1,2,4-oxadiazole-4-oxides. Consideration of the nitronate-like resonance structure of nitrodiazo compounds led to an examination of the photochemistry of nitronates with -leaving groups. Photolysis of such nitronates has been shown to generate an acyl nitroso species along with a carbene intermediate. Nanosecond time-resolved infrared (TRIR) spectroscopy has been used to detect photogenerated acyl nitroso compounds directly and to examine their reaction kinetics with amines and thiols. The mechanism of acyl nitroso aminolysis by primary amines involves general base catalysis, while the mechanism of aminolysis by secondary amines is strictly bimolecular. Thiols do not seem to be reactive with acyl nitroso compounds on the microsecond time scale, but thiolates are quite reactive. The reaction between benzoyl nitroside and an organic-soluble thiolate, tetrabutylammonium dodecanethiolate, proceeds via a proposed tetrahedral intermediate, which is observable by TRIR spectroscopy.

Cycloadditions of nitrile oxides to amidoximes. A general synthesis of 3,5-disubstituted 1,2,4-oxadiazole-4-oxides

The cycloaddition of nitrile oxides to amidoximes is a general method for the synthesis of 3,5-disubstituted 1,2,4-oxadiazole-4-oxides with the same or different substituents. The yields are only moderate since an equivalent amount of the nitrile oxide is consumed by reaction with the amine released in the fragmentation of the primary cycloadducts and reforms the amidoxime. With excess nitrile oxides the 1,2,4-oxadiazole-4-oxides undergo a disproportionation reaction to yield nitroso carbonyl intermediates and 1,2,4-oxadiazoles.