52755-67-6

Upstream product

• 124-38-9 carbon dioxide 
• 16205-14-4 2-Methyl-3-phenyl-2H-azirine 
• 1532565-46-0 (1-azido-2-iodopropyl)benzene 
• 873-66-5 1-propenylbenzene 
• 79999-05-6 2-methyl-4-phenyl-4-(2,3-diphenyl-1-methyl-2-cyclopropen-1-yl)-Δ²-oxazolin-5-one 
• 16205-14-4 2-phenyl-3-methylazirine 

Downstream Products

• 4855-25-8 2-methyl-4-ethyl-4-phenyl-Δ²-oxazolin-5-one 
• 79402-67-8 2-methyl-4-(3-methyl-2-butenyl)-4-phenyl-Δ²-oxazolin-5-one 
• 84537-27-9 2-phenyl-4-methyl-4-(1,3-diphenyl-2-methyl-2-cyclopropen-1-yl)-Δ²-oxazolin-5-one 
• 79998-99-5 2-phenyl-4-methyl-4-(1-methyl-2,3-diphenyl-2-cyclopropen-1-yl)-Δ²-oxazolin-5-one 
• 79999-05-6 2-methyl-4-phenyl-4-(2,3-diphenyl-1-methyl-2-cyclopropen-1-yl)-Δ²-oxazolin-5-one 
• 84537-26-8 2-methyl-4-phenyl-4-(1,2,3-triphenyl-2-cyclopropen-1-yl)-Δ²-oxazolin-5-one 
• 79402-73-6 2-methyl-4-benzyl-4-phenyl-Δ²-oxazolin-5-one 
• 79402-65-6 2-methyl-4-allyl-4-phenyl-Δ²-oxazolin-5-one 
• 46181-30-0 6-methyl-2-phenylpyridine 
• 56434-99-2 2-methyl-6-phenyl-pyridine; picrate 
• 84537-30-4 N-(α-allyl-benzylidene)acetamide 
• 79998-98-4 2-methyl-2-(1,2,3-triphenyl-2-cyclopropen-1-yl)-4-phenyl-Δ³-oxazolin-5-one 
• 79402-71-4 N-(α-ethylbenzylidene)acetamide 
• 79402-70-3 N-(α-prenylbenzylidene)acetamide 

Relevant academic research and scientific papers

Comparison of the photochemistry of 3-methyl-2-phenyl-2h-azirine and 2-methyl-3-phenyl-2h-azirine

Photolysis of 3-methyl-2-phenyl-2H-azirine (1a) in argon-saturated acetonitrile does not yield any new products, whereas photolysis in oxygen-saturated acetonitrile yields benzaldehyde (2) by interception of vinylnitrene 5 with oxygen. Similarly, photolysis of 1a in the presence of bromoform allows the trapping of vinylnitrene 5, leading to the formation of 1-bromo-1-phenylpropan-2-one (4). Laser flash photolysis of 1a in argon-saturated acetonitrile (? = 308 nm) results in a transient absorption with ?max at 440 nm due to the formation of triplet vinylnitrene 5. Likewise, irradiation of 1a in cryogenic argon matrixes through a Pyrex filter results in the formation of ketene imine 11, presumably through vinylnitrene 5. In contrast, photolysis of 2- methyl-3-phenyl-2H-azirine (1b) in acetonitrile yields heterocycles 6 and 7. Laser flash photolysis of 1b in acetonitrile shows a transient absorption with a maximum at 320 nm due to the formation of ylide 8, which has a lifetime on the order of several milliseconds. Similarly, photolysis of 1b in cryogenic argon matrixes results in ylide 8. Density functional theory calculations were performed to support the proposed mechanism for the photoreactivity of 1a and 1b and to aid in the characterization of the intermediates formed upon irradiation.

Aza Cope Rearrangements in the Cyclopropenyl-and Allyl-Substituted Δ2-Oxazolinone Systems

The scope of the thermal and photochemical reorganization reactions of a number of cyclopropenyl- and allyl- substituted oxazolinones has been examined.These systems undergo a facile sigmatropic rearrangement in accord with orbital symmetry predictions. 2-Methyl-4-allyl-Δ2-oxazolinones were found to undergo a 3,3-sigmatropic allyl shift on thermolysis to give the Δ3-oxazolinone isomer.In contrast, on direct irradiation the 2-methyl-4-allyl-Δ3-oxazolinones undergo a 1,3-allyl shift to give the Δ2-isomer.The 4,4-disubstituted Δ2-oxazolinones undergo decarbonylat ion either on irradiation or by flash vacuum pyrolysis to give acetimides.The acetimides formed were easily hydrolyzed to give the corresponding ketones.The excited-state behavior of the 2-phenyl-4-methyl-Δ2-oxazolinone system was found to be markedly different from that encountered with the 2-methyl-4-phenyl-substituted isomer.The rationale for the difference in behavior is discussed.