112156-87-3Relevant articles and documents
PHOTOOXIDATION OF SOME MESOIONIC AND RELATED SYSTEMS
Kato, Hiroshi,Tani, Kazue,Kurumisawa, Haruki,Tamura, Yoshiko
, p. 717 - 720 (1980)
Photooxidation of several mesoionic compounds gave ring cleavage products, some of which were apparently formed via the endoperoxides of the mesoionic rings.Photooxidation of a Δ2-oxazolin-4-one and Δ2-thiazolin-4-one gave the corresponding 4,4'-bisoxa- and bisthiazolinone in dichloromethane, whereas the former gave benzamide in dimethylformamide.
PHOTOCHEMICAL AND THERMAL REACTIONS OF HETEROCYCLES. IV. PHOTO-OXIDATION REACTIONS OF MESOIONIC DITHIOLIUMOLATE, THIAZOLIUMOLATE, AND RELATED HETEROCYCLES. SOLVENT EFFECTS ON THE COURSE OF THE PHOTO-OXIDATION
Kato, Hiroshi,Tani, Kazue,Kurumisawa, Haruki,Tamura, Yoshiko
, p. 1313 - 1322 (2007/10/02)
Photo-oxidation of mesoionic 1,3-dithiolium-4-olates (1) gave diacyl disulfide (2), and that of a mesoionic thiazolium-4-olate (6) and oxazolium-5-olate (9) gave diacylamides as the main products.The formation of these products was rationalized by a route involving fragmentation of the corresponding endoperoxides, which are formed by cycloaddition of singlet oxygen on the mesoionic rings.Photo-oxidation of 5(4H)-oxazolones (12) and a 5(4H)-thiazolone (17) in dichloromethane gave the corresponding dehydro-dimers, while that of the former in dimethylformamide gave mainly diacylamides.The acylamides were considered to arise via the endoperoxides of the mesoionic tautomers.