Photooxygenation of aziridines and some potential azomethine ylides

Journal Article · Fri Sep 14 04:00:00 EDT 1979 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo01333a002· OSTI ID:5130079

Bhat, V ^[1]; George, M V

---

1. Indian Inst. of Technology, Kanpur, India

Sensitized photooxygenations of a few bicyclic aziridines and some potential azomethine ylides have been investigated. The photooxygenation of 1-cyclohexyl-6-(cyclohexylimino)-1a-phenylindano(1,2-b)aziridine gave a 51% yield of 2-cyclohexyl-3-hydroxy-3-phenylphthalimidine. The photoxygenation of endo-2,4,6-triphenyl-1,3-diazabicyclo(3.1.0)hex-3-ene, on the other hand, gave a mixture of products consisting of benzaldehyde (5%), benzoic acid (5, 16%), and benzamide (19, 7%). Other substrates that we have examined include 2,3-dihydro-5,6-diphenylpyrazine (22), cis-2,4,5-triphenylimidazoline (33a), and 4-benzoyl-3-cyclohexyl-5-(cis-1,2-diphenylvinyl-2-phenyloxazoline (42). The photooxygenation of 22, for example, gave a 22% yield of 1,3-dibenzoylurea, whereas 33a, under analogous conditions, gave a mixture of products consisting of 2,5,5-triphenylimidazolin-4-one (7%), dibenzamide (8%), and 19 (21%). The photooxygenation of 42 gave a mixture of products consisting of 5 (51%) and N-cyclohexylbenzamide (19%), whereas the direct photolysis of 42 under nitrogen atmosphere gave a 65% yield of 3,5,6-triphenyl-2H-pyran-2-one. Reasonable mechaisms have been suggested for the formation of the different products in these reactions.

• OSTI ID: 5130079
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 44:19; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400500* -- Photochemistry
ALDEHYDES
AROMATICS
BENZALDEHYDE
BENZOIC ACID
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
DECOMPOSITION
ELEMENTS
HETEROCYCLIC COMPOUNDS
MONOCARBOXYLIC ACIDS
NONMETALS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXYGEN
PHOTOCHEMICAL REACTIONS
PHOTOLYSIS