- Synthesis of azirines containing aldehyde functionality and their utilization as synthetic tools for five membered oxazoles and isoxazoles
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(Chemical Equation Presented) A simple and useful procedure for the synthesis of azirines containing aldehyde functionality from open chain bromo/chloro-aldehydes at room temperature is reported. The scope of the ring expansion reaction of a number of 3-s
- Brahma, Sulagna,Ray, Jayanta K.
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p. 311 - 317
(2008/09/20)
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- Photochemistry of 4- and 5- phenyl substituted isoxazoles
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5-Phenylisoxazole (4) and 4-phenylisoxazole (22) underwent phototransposition to 5-phenyloxazole (5) and 4-phenyloxazole (24) respectively. Labeling with deuterium or methyl confirmed that these phototrans-positions occurred via the P4 pathway which involves only interchange of the N2 and C3 ring position. Thus, 4-deuterio-5-phenylisoxazole (4-4d), 4-methyl-5-phenylisoxazole (10), and 5-methyl-4-phenylisoxazole (23) phototransposed to 4-deuterio-5-phenyloxazole (5-4d), 4-methyl-5-phenyloxazole (11), and 5-methyl-4-phenyloxazole (25) respectively. In addition to phototransposition, isoxazoles 4, 10, and 23 also underwent photo-ring cleavage to yield benzoylacetonitrile (9), α-benzoylpropionitrile (15), and aceto-α-phenyl-acetonitrile (26) respectively. Irradiation of 5-phenyl-3-(trifluoromethyl)isoxazole (16) in acetonitrile led to 5-phenyl-2-(trifluoromethyl)oxazole (17), the P4 phototransposition product. Irradiation of 16 in methanol led to a substantial decrease in the yield of 17 and to the formation of a mixture of (E) and (Z)-2-methoxy-2- (trifluoromethyl)-3-benzoylaziridines 18a and 18b.
- Pavlik, James W.,St. Martin, Heather,Lambert, Karen A.,Lowell, Jennifer A.,Tsefrikas, Vikki M.,Eddins, Cheryl K.,Kebede, Naod
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p. 273 - 281
(2007/10/03)
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