An examination of the affect of the epoxide stereochemistry in the nitrogen extrusion from exo- And endo-6,7-diazo-3-oxotricyclo[3.2.2.02,4]Non-6-ene

Article abstract of DOI:10.1016/S0040-4039(00)97822-5

The exo and endo isomers of 6,7-diazo-3-oxotricyclo[3.2.2.0^2,4]non-6-ene have been prepared and their extrusion of nitrogen examined. The exo isomer 10 underwent the expected homo-retro-Diels-Alder reaction at room temperature to give 4,5-dihydrooxepin (11), but the endo isomer extruded nitrogen at>180 °C to give cyclohexenone.