Photooxygenations of sydnones and azomethine imines

Journal Article · Fri Aug 17 04:00:00 EDT 1979 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo01331a001· OSTI ID:6050623

Bhat, V ^[1]; Dixit, V M; Ugarker, B G; Trozzolo, A M; George, M V

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1. Indian Inst. of Techology, Kanpur

Sensitized photooxygenations of a few sydnones and azomethine imines have been studied. The photooxygenation of 3,4-diphenylsydnone, for example, gave a 25% yield of ..cap alpha..,..beta..-dibenzoylphenylhydrazine as the only isolable product, whereas the photooxygenation of 4-phenyl-3-p-tolylsydnone resulted in the formation of a mixture of products containing ..cap alpha..,..beta..-dibenzoyl-p-tolylhydrazine (8%) and 4,5-diphenyl-2-p-tolyl-1,2,3-triazole (8%). Under analogous conditions, 3-phenyl-4-p-tolylsydnone gave a mixture of products consisting of ..cap alpha..,..beta..-di-p-toluylphenylhydrazine (10%) and 2-phenyl-4,5-di-p-tolyl-1,2,3-triazole (1%). Irradiation of 3-phenyl-4-p-tolylsydnone in either benzene or methanol and in the absence of any oxygen gave the 2-phenyl-4,5-di-p-tolyl-1,2,3-triazole as the only isolable product. Similarly, the photooxygenation of 3-methyl-4-phenylsydnone in methanol gave a mixture of benzoic acid (10%) and ..cap alpha..,..beta..-dibenzoylmethylhydrazine (5%), whereas irradiation of 3-methyl-4-phenylsydnone in benzene gave a 10% yield of 4-methyl-2-phenyl-..delta../sup 2/-1,3,4-oxadiazolin-5-one. The photooxygenation of an azomethine imine, namely, C-biphenylene-N/sup ..cap alpha../-(4-chlorophenyl)-N/sup ..beta../-cyanoazomethine imine, gave a 78% yield of 9-fluorenone. Reasonable mechanisms have been suggested for the formation of the various products in these reactions. 5 figures.

• OSTI ID: 6050623
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 44:17; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
400500* -- Photochemistry
ALCOHOLS
AROMATICS
AZINES
AZO COMPOUNDS
AZOLES
BENZENE
BENZOIC ACID
CARBOXYLIC ACIDS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMICAL SHIFT
CONDENSED AROMATICS
DATA
DATA FORMS
EXPERIMENTAL DATA
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROXY COMPOUNDS
IMINES
INFORMATION
INFRARED SPECTRA
ISOLATED VALUES
KINETICS
MAGNETIC RESONANCE
METHANOL
MONOCARBOXYLIC ACIDS
NUCLEAR MAGNETIC RESONANCE
NUMERICAL DATA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SOLVENTS
OXIDATION
PHOTOCHEMICAL REACTIONS
REACTION KINETICS
RESONANCE
SOLVENTS
SPECTRA
TRIAZOLES
ULTRAVIOLET SPECTRA
YIELDS