24516-62-9Relevant academic research and scientific papers
Heterocyclisations radicalaires d'aminothiols ethyleniques. I. Generalites sur la formation de composes thiazolidiniques
Kaafarni, Mustapha,Crozet, Michel P.,Surzur, Jean-Marie
, p. 449 - 457 (2007/10/02)
Free radical initiation or photolysis of N-allyl-2-aminothiols 1 leads not only to a mixture of heterocyclic compounds b and c resulting from intramolecular addition of the thiyl radical to the terminal double bond but also to 2-alkyl-thiazolidines a.The ratios of these two types of heterocyclic compounds are very sensitive to the experimental conditions and the structures of the reagents.Compounds b and c are the major ones at low reaction temperature, low aminothiol concentration, in a poor hydrogen-donating solvent and with starting compounds 1 containing a tertiary amino group.Thiazolidines a are the major products at high reaction temperature, high aminothiol concentration, in a good hydrogen-donating solvent and with starting compounds 1 containing a secondary amino group.Thiazolidines a are assumed to arise from intramolecular allylic hydrogen abstraction by the thiyl radical.This unusual reactivity of the thiyl radical towards hydrogen abstraction (rather than addition) is discussed.
