The chemistry of azidotropones. Part III. Formation and decomposition of Δ2-triazolines derived from norbornene

Abstract

1,3-Cycloadditions of 2-, 3-, and 4-azidotropone to norbornene have been studied. The products formed on thermolysis of the 1-substituted 1,2,3-Δ²-triazolines so obtained have been characterised as derivatives of syn-7-aminonorbornene and 3-azatricyclo[3,2,1,0^2,4]octane. Notable differences in the rates of formation and stabilities of the triazolines, and in the relative proportions of the two types of thermolysis product, are observed between the compounds derived from 2-azidotropone on the one hand, and those from the 3- and 4-isomers on the other.