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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.