title: Generation and contrasting gas-phase reactivity of 2-(2-alkenylpyrrol-1-yl)phenoxyl and thiophenoxyl radicals.
abstract: The pyrrolylacrylates 9 and 10 were synthesised and subjected to flash vacuum pyrolysis (FVP) at 650-700 degrees C to generate the radicals 11 and 18, respectively. The phenoxyl 11 underwent hydrogen capture to give a mixture of the phenol 12 and the pyrrolobenzoxazine 13 in low yields, which were also obtained by a Wittig reaction of the 2-formylpyrrole 14. The thiophenoxyl 18 gave a single major product in 41% yield which was identified as the pyrrolo[1,2-a]quinoline 17 by a sequence of NMR experiments. A mechanism for the formation of 17 by a rearrangement-sulfur extrusion sequence is proposed.
authors.affiliation: Department of Chemistry, University of Wales Swansea, UK.
authors.forename: J I G
authors.initials: JI
authors.lastname: Cadogan
authors.forename: Chandralal M
authors.initials: CM
authors.lastname: Hewage
authors.forename: Hamish
authors.initials: H
authors.lastname: McNab
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Macpherson
authors.forename: Iain S
authors.initials: IS
authors.lastname: Nicolson
authors.forename: David
authors.initials: D
authors.lastname: Reed
authors.forename: Ian H
authors.initials: IH
authors.lastname: Sadler