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Photochemische Cycloadditionen von 3‐Phenyl‐2H‐azirinen mit aktivierten Doppelbindungen . Vorläufige Mitteilung
Author(s) -
Jackson B.,
Märky M.,
Hansen H.J.,
Schmid H.
Publication year - 1972
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.19720550318
Subject(s) - chemistry , nitrile , medicinal chemistry , irradiation , stereochemistry , organic chemistry , nuclear physics , physics
Irradiation of 2‐methyl‐ ( 1a ), 2,2‐dimethyl‐ ( 1b ) and 2,3‐diphenyl‐2 H ‐azirine ( 1c ) in the presence of diethyl mesoxalate yields the corresponding 4‐phenyl‐5,5‐diethoxycarbonyl‐3‐ oxazolines 3a–c . Similar cycloadducts are observed (cf. 6 ) by irradiation of 1b and 1c in the presence of trifluoroacetophenone. When ethyl cyanoformate is used as trapping agent photolysis of 1b or 1c leads to cycloadducts with the carbonyl and nitrile group, respectively which are present in the cyanoformate.