title: Synthesis and X-ray structural studies of a substituted 2,3,4,5-tetrahydro-1H-3-benzazonine and a 1,2,3,5-tetrahydro-4,3-benzoxazonine.
abstract: Using a common 1-(1-phenylethenyl)-1,2,3,4-tetrahydroisoquinoline precursor to the required ylide or N-oxide intermediate, the Stevens [2,3] and analogous Meisenheimer [2,3] sigmatropic rearrangements have been applied to afford concise syntheses of phenyl -substituted representatives of each of the reduced 1H-3-benzazonine and 4,3-benzoxazonine systems, respectively. Single crystal X-ray structure determinations were employed to define the conformational characteristics for each ring type.
authors.affiliation: Department of Chemistry, University of Tasmania, Hobart, Tas. 7001, Australia. SBAILEY3@its.jnj.com.
authors.forename: Timothy S
authors.initials: TS
authors.lastname: Bailey
authors.affiliation: School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia. john_bremner@uow.edu.au.
authors.forename: John B
authors.initials: JB
authors.lastname: Bremner
authors.affiliation: School of Chemistry and Biochemistry M310, The University of Western Australia, Crawley, WA 6009, Australia. brian.skelton@uwa.edu.au.
authors.forename: Brian W
authors.initials: BW
authors.lastname: Skelton
authors.affiliation: School of Chemistry and Biochemistry M310, The University of Western Australia, Crawley, WA 6009, Australia. allan.white@uwa.edu.au.
authors.forename: Allan H
authors.initials: AH
authors.lastname: White
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D066244:Proton Magnetic Resonance Spectroscopy
chemical_list: D006571:Heterocyclic Compounds; D006574:Heterocyclic Compounds, 2-Ring