Photoinduzierte Cycloadditionen von 3‐Benzyl‐2 H ‐azirin | Zendy

Orahovats Alexander | Zendy; Jackson Barry | Zendy; Heimgartner Heinz | Zendy; Schmid Hans | Zendy

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Photoinduzierte Cycloadditionen von 3‐Benzyl‐2 H ‐azirin

Author(s) -

Orahovats Alexander,

Jackson Barry,

Heimgartner Heinz,

Schmid Hans

Publication year - 1973

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19730560621

Subject(s) - chemistry , trifluoroacetic acid , pentane , benzene , medicinal chemistry , trifluoromethyl , irradiation , photochemistry , polymer chemistry , organic chemistry , alkyl , physics , nuclear physics

Irradiation of 2‐azido‐3‐phenyl‐propene ( 5 ) in pentane or benzene solution with a high pressure lamp (pyrex filter) yields 3‐benzyl‐2 H ‐azirin ( 6 ), which on further irradiation behind quartz or vycor in the presence of trifluoroacetic acid methylester or carbon dioxide yields 4‐benzyl‐5‐methoxy‐5‐trifluoromethyl‐3‐oxazolin ( 8 ) and 4‐benzyl‐3‐oxazolin‐5‐one ( 9 ), respectively (scheme 2). A small amount of 3‐phenylacetonitrile is also formed.

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