h o l e s are five-membered ring heterocycles which may be considered as ring-closed forms of conjugated 1,9dipoles (Scheme l).' The equilibrium positions are usually shifted towards the aromatic compounds, except for a-diazoketones (or esters) and acyl azides (6 and 8, X = 0) of which the corresponding heterocycles are unknown.* a-Diazothioketones and thioacyl azides, on the contrary, only exist as transient intermediates which cyclize to thiadiazoles and thiatriazoles respectively (5 and 7, X = S).3 lminodiazomethanes and iminoazides (6 and 8, X = NR) most often cyclize to triazoles and tetrazoles (5 and 7, X = NR), but they can be stabilized in the open-chain form by introducing strong electron-withdrawing substituents at the imine n i t r~g e n .~