136019-61-9Relevant articles and documents
On the Route to the Photogeneration of Heteroaryl Cations. the Case of Halothiophenes
Raviola, Carlotta,Chiesa, Francesco,Protti, Stefano,Albini, Angelo,Fagnoni, Maurizio
, p. 6336 - 6342 (2016)
2-Chloro-, 2-bromo-, and 2-iodothiophenes undergo photochemical dehalogenation via the triplet state. In the presence of suitable π-bond nucleophiles, thienylation occurs with modest yield from chloro and bromo derivatives (via photogenerated triplet 2-thienyl cation). Specific trapping by using oxygen along with computational analysis carried out by means of a density functional method support that, in the case of iodo derivatives, homolytic thienyl-I bond fragmentation occurs first and heteroaryl cations are formed by electron transfer within the triplet radical pair, thus opening an indirect access to such cations.