903901-01-9Relevant articles and documents
Generation and contrasting gas-phase reactivity of 2-(2-alkenylpyrrol-1-yl) phenoxyl and thiophenoxyl radicals
Cadogan,Hewage, Chandralal M.,McNab, Hamish,MacPherson, Andrew D.,Nicolson, Iain S.,Reed, David,Sadler, Ian H.
, p. 2446 - 2451 (2006)
The pyrrolylacrylates 9 and 10 were synthesised and subjected to flash vacuum pyrolysis (FVP) at 650-700 °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. The Royal Society of Chemistry 2006.