Positional selectivity in the rearrangement of 7-formyl and 7-vinyl norcaradienes; evidence for 3,5-sigmatropy
Abstract
The 7-formylnorcaradiene (1; X = O, R = Me) rearranges at 40 °C to the dihydrobenzofuran (4; X = O, R = Me) and the 7-vinylnorcaradiene (1; X =E-CHCO2Et, R = Me) rearranges to the dihydroindene (9), evidence for 3,5-rather than 1,3-sigmatropy in both processes.