128654-38-6Relevant articles and documents
Reactions of Aryl Azides with Alkenes in the Presence of Aluminium Trichloride. Formation of Novel Aziridines fused to Seven- and Eight-membered Rings
Takeuchi, Hiroshi,Shiobara, Yukihiko,Kawamoto, Hideyuki,Koyama, Kikuhiko
, p. 321 - 327 (2007/10/02)
Reactions of aryl azides (1) with cyclohexene gave 3-(arylamino)cyclohexenes (2) and trans-1-chloro-2-(arylamino)cyclohexanes (3), whereas that of (1) with cycloheptene or cis-cyclo-octene afforded novel aziridines, 8-aryl-8-azabicyclooctanes (4), or 9-aryl-9-azabicyclononanes (5), respectively.The reaction of phenyl azide (1a) with cis-4-methylpent-2-ene yielded 3-anilino-2-chloro-4-methylpentane (10), but that with the trans-alkene gave 4-anilino-2-methylpent-2-ene (7) and 3-anilino-4-methylpent-1-ene (8).The similar reaction of (1) with 3-trimethylsilylcyclohexene or 3-trimethylsilyl-cis-cyclo-octene produced only (2) or 3-(arylamino)-cis-cyclo-octenes (2').The formation of the aziridines or the ring-opened products was explained by a mechanism via an aziridinium-AlCl3 complex formed from an azide-AlCl3 complex.