title: Acid-mediated ring-expansion reaction of N-aryl-2-vinylazetidines: synthesis and unanticipated reactivity of tetrahydrobenzazocines.
abstract: The aza-Clasen rearrangement of N-aryl-2-vinylazetidines has been explored. N-Aryl-2-vinylazetidines were transformed to corresponding tetrahydrobenzazocines in good yields. Unexpectedly, the tetrahydrobenzazocine was unstable and readily isomerized to vinyltetrahydroquinoline in the presence of acid. The mechanism of this ring contraction was studied in detail.
authors.affiliation: Department of Chemistry, Faculty of Science, Tokyo University of Science , Kagurazaka, Shinjuku, Tokyo 162-8601, Japan.
authors.forename: Tomoaki
authors.initials: T
authors.lastname: Shimizu
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Koya
authors.forename: Ryu
authors.initials: R
authors.lastname: Yamasaki
authors.forename: Yuichiro
authors.initials: Y
authors.lastname: Mutoh
authors.forename: Isao
authors.initials: I
authors.lastname: Azumaya
authors.forename: Kosuke
authors.initials: K
authors.lastname: Katagiri
authors.forename: Shinichi
authors.initials: S
authors.lastname: Saito
mesh_terms: D002384:Catalysis; D003496:Cyclazocine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D007536:Isomerism; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D011804:Quinolines; D014753:Vinyl Compounds; D003496:Cyclazocine