Non-benzenoid aromatic azides

Tropone may be represented structurally as a resonance hybrid (159) and the weight of evidence suggests 159b as most nearly representing the true structure The resemblance to heteroaromatic 

The structure of tropyl azide, which is synthesized by the action of azide ion on tropylium perchlorate , may be represented as the covalent azidocycloheptatriene (161), the non-benzenoid aromatic tropylium salt with azide as the counter-ion (162), or an equilibrium mixture of the two. Spectroscopic studies by Wulfman and colleagues indicate that in non-polar solvents such as carbon 

Interest in the chemistry of tropyl azide stems from the prediction that a multiplicity of products might arise by unimolecular decomposition or self-reactions. Wulfman and Ward have in fact presented spectroscopic evidence for the formation of the unique sandwich compound (163), resulting from the interaction of tropyl azide and the derived 1-aza-tricyclo [3,3,0,0 ] octa-3,6-diene (164). 

Azidoferrocenes have been synthesized by treating bromoferrocenes with azide ion and cupric bromide in dimethylformamide . Thus ferrocenyl azide (165) was obtained in 98% yield from bromoferrocene and 1, T-ferrocenylene diazide (166) was prepared from the corres- 

---

The photochemistry of 2-azidotropone (142) a non-benzenoid aromatic azide, was investigated by Hobson and Malpass . The primary reaction product is a ketene (143) which in the absence of... 

---