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Photochemical transformations of 4,5‐diaryl‐4‐oxazolin‐2‐one protecting groups
Author(s) -
Guziec Frank S.,
Tewes Edwin T.
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170837
Subject(s) - chemistry , benzamide , protecting group , photooxygenation , photochemistry , photodissociation , methanol , cleavage (geology) , medicinal chemistry , organic chemistry , alkyl , singlet oxygen , geotechnical engineering , fracture (geology) , engineering , oxygen
The photochemical cleavage of 4,5‐diaryl‐4‐oxazolin‐2‐one protecting groups is discussed as an alternative to reduction or chemical oxidation of the heterocyclic system. Ultraviolet irradiation in air of oxazolinone ( 1 ) in methanol leads to photooxygenation of the protecting group, affording the corresponding benzamide and benzoate ester. Reduction of the intermediate photoproduct leads to complete removal of the protecting group. A mechanism for this photolysis is proposed and evidence in support of this mechanism is reported.