68004-05-7Relevant articles and documents
Photochemistry of 3- and 5-phenylisothiazoles. Competing phototransposition pathways
Pavlik, James W.,Tongcharoensirikul, Pakamas
, p. 3626 - 3631 (2000)
5-Phenylisothiazole undergoes phototransposition via the electrocyclic ring closure-heteroatom migration pathway and by the N2-C3 interchange reaction pathway. The latter route is enhanced by the addition of triethylamine (TEA) to the reaction medium and by increasing the polarity of the solvent. In addition to phototransposition, 5-phenylisothiazole also undergoes photocleavage to 2-cyano-1-phenylethenethiol which was trapped by reaction with benzyl bromide to yield 2-cyano-1-phenylethen-1-ylbenzyl thioether. 3-Phenylisothiazole also phototransposes by both reaction pathways, but the product distribution is not affected by the addition of TEA or by changing the solvent polarity.
