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Photochemie von Benzisoxazolen. (vorläufige Mitteilung)
Author(s) -
Heinzelmann W.,
Märky M.
Publication year - 1974
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.19740570212
Subject(s) - chemistry , acetonitrile , solvent , yield (engineering) , photodissociation , alkyl , hexane , photochemistry , solvent polarity , medicinal chemistry , organic chemistry , metallurgy , materials science
The photochemical behaviour of benzisoxazoles 1 is remarkably solvent‐dependent: Irradiation in H 2 O or CH 3 O or CH 3 OH leads to benzoxazoles 2 in a virtually quantitative yield. However, at low concentrations of H 2 O or CH 3 OH in acetonitrile or hexane, photolysis of 3‐alkyl‐benzisoxazoles 1b–1e yields salicylamides 4 and salicylesters 5 , while under these conditions o ‐cyanophenol ( 3a ) is the only photoproduct of benzisoxazole ( 1a ). The course of these photochemical reactions is discussed from the standpoint of solvent‐dependence, multiplicity and the behaviour at low temperatures.