Sensitized photooxygenations of. delta. /sup 2/-oxazolin-5-ones and related studies

Journal Article · Thu Nov 08 23:00:00 EST 1979 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo01337a033· OSTI ID:5548978

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

---

1. Indian Inst. of Tech., Kanpur

Sensitized photooxygenations of a few ..delta../sup 2/-oxazolin-5-ones such as 2,4-diphenyl-..delta../sup 2/-oxazolin-5-one (3a), 4-benzyl-2-phenyl-..delta../sup 2/-oxazolin-5-one (3b), and 4-benzylidene-2-phenyl-..delta../sup 2/-oxazolin-5-one (17) have been studied, using Rose Bengal as a sensitizer. The photoxygenation of 3a in a mixture of benzene and methanol for 0.25 h gave a mixture of bi-4,4'-(2,4-diphenyl-..delta../sup 2/-oxazolin-5-one) (9a, 44%) and benzamide (28%), whereas the photooxygenation of 3a in methanol for 0.5 h gave a mixture of dibenzamide (8a, 40%) and benzamide (49%). In contrast, the irradiation of 3a in either benzene or cyclohexane gave only benzamide. Nickel peroxide oxidation of 3a gave a 38% yield of the bioxazolinone 9a. Direct irradiation of 9a in either benzene or acetone gave benzamide, whereas the thermolysis of 9a in refluxing o-dichlorobenzene gave a 3% yield of 2,3,5,6-tetraphenylpyrazine (16). Photooxygenation of 3b gave a 42% yield of N-benzoylphenylacetamide (8b), whereas the direct irradiation of 3b gave only benzamide. Nickel peroxide oxidation of 3b gave bi-4,4'-(4-benzyl-2-phenyl-..delta../sup 2/-oxazolin-5-one) (9b, 40%). Direct irradiation of 9b gave exclusively benzamide. The photooxygenation of 17 in methanol gave a mixture of the ..cap alpha..-benzamidocinnamate 18 (53%) and benzamide (29%), whereas the direct irradiation of 17 gave a mixture of ..cap alpha..-benzamidocinnamic acid (20) (31%) and benzamide (52%). Reasonable mechanisms have been suggested for the formation of the different products in these reactions.

• OSTI ID: 5548978
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 44:23; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400500* -- Photochemistry
ACETONE
ALCOHOLS
ALKANES
AROMATICS
AZOLES
BENZENE
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
CHEMISTRY
CYCLOALKANES
CYCLOHEXANE
DYES
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROXY ACIDS
HYDROXY COMPOUNDS
INDICATORS
IRRADIATION
KETONES
METHANOL
NICKEL COMPOUNDS
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXAZOLES
OXIDATION
PHOTOCHEMICAL REACTIONS
PHOTOCHEMISTRY
REAGENTS
ROSE BENGAL
SENSITIZERS
TRANSITION ELEMENT COMPOUNDS