89986-65-2Relevant academic research and scientific papers
On the Mechanism of the Formation of Rearrangement Products in the Addition of Arenesulfenyl Chloride and 4-Phenyl-4H-1,2,4-triazole-3,5-dione to Benzonorbornadienes
Adam, Waldemar,Carballeira, Nestor,Scheutzow, Dieter,Peters, Karl,Peters, Eva-Maria,Schnering, Hans Georg von
, p. 1139 - 1152 (2007/10/02)
On the basis of product and rate studies the similarity in the electrophilic addition of phenyltriazolediones (PTAD) and the arenesulfenyl chlorides 10 and 11 to benzonorbornadienes 1, 8, and 9, giving the rearrangement products 2 and 6, respectively, is being recognized.In analogy to the established mechanism involving three-center electrophilic attack for the arenesulfenyl chloride reaction, the PTAD reaction is proposed to proceed via the aziridinium ion 4 as intermediate.The lack of trapping, of regioselectivity and of formation of addition product in the case ofPTAD is interpreted in terms of electronic and steric effects on the dipolar aziridinium species. - An X-ray analysis of the addition product 17, derived from 9 and 11, is reported.
