Preparation and thermal rearrangement of an aza-analogue of 4,5-homotropone (bicyclo[5.1.0]octa-3,5-dien-2-one)
Abstract
Phthalimidonitrene adds to the 4,5-rather than the 2,3-double bond of trophone in accord with addition via the syn-arrangement (6) stabilised by two secondary interactions; thermal and photochemical rearrangement of the 8-azabicyclo[5.1.0]octadienone derivative (2; X = NR) at 80 °C proceeds by apparent C–C bond cleavage, to give (3).