63115-45-7

Upstream product

• 51029-28-8 10-(1-oxoethyl)-9,10-dihydro-9,10-dimethyl-10,9-(epoxyimino)anthracene 

Downstream Products

• 74326-69-5 N-Hydroxy-N-(2-methyl-cyclohex-2-enyl)-acetamide 
• 74326-74-2 N-Hydroxy-N-(1-isopropenyl-octyl)-acetamide 
• 74326-71-9 N-Hydroxy-N-(2-methyl-1-phenyl-allyl)-acetamide 
• 74326-72-0 N-Hydroxy-N-[2-(4-methoxy-phenyl)-cyclohex-2-enyl]-acetamide 
• 74326-67-3 N-Cyclohex-2-enyl-N-hydroxy-acetamide 
• 51029-28-8 12-acetyl-9,10-dimethyl-9,10-dihydro-10,9-oxaazaethano-anthracene 
• 77803-76-0 N-acetyl-2-oxa-3-azabicyclo<2.2.2>oct-5-ene 
• 64-19-7 acetic acid 
• 74326-70-8 N-Hydroxy-N-(2-phenyl-cyclohex-2-enyl)-acetamide 

Relevant academic research and scientific papers

Nitrosocarbonyl release from O-substituted hydroxamic acids with pyrazolone leaving groups

A new class of nitrosocarbonyl precursors, O-substituted hydroxamic acids with pyrazolone leaving groups (OHPY), is described. These compounds generate nitrosocarbonyl intermediates, which upon hydrolysis release nitroxyl (azanone, HNO) under physiologically relevant conditions. Pyrazolones have been used to confirm the generation of nitrosocarbonyls by competitive trapping to form isomeric N-substituted hydroxamic acids (NHPY) via an N-selective nitrosocarbonyl aldol reaction. The rate of nitrosocarbonyl release from OHPY donors is impacted by donor substituents, including the pyrazolone leaving group.

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.