Diazo

Some of the most stable diazo compounds are α-diazo-β-diketones and α-diazo-β-diesters, in which the electron density is further delocalized into an electron-withdrawing carbonyl group.

A group of isomeric compounds with only few similar properties are the diazirines, where the carbon and two nitrogens are linked as a ring.

Diazo compounds were first produced by Peter Griess who had discovered a versatile new chemical reaction, as detailed in his 1858 paper "Preliminary notice on the influence of nitrous acid on aminonitro- and aminodinitrophenol.

[4][5] Alpha-acceptor-substituted primary aliphatic amines R-CH2-NH2 (R = COOR, CN, CHO, COR) react with nitrous acid to generate the diazo compound.

In diazo transfer certain carbon acids react with tosyl azide in the presence of a weak base like triethylamine or DBU.

[10][11] The mechanism involves attack of the enolate at the terminal nitrogen, proton transfer, and expulsion of the anion of the sulfonamide.

Use of the β-carbonyl aldehyde leads to a deformylative variant of the Regitz transfer, which is useful for the preparation of diazo compounds stabilized by only one carbonyl group.

It involves a sequence of enzyme-mediated redox reactions to generate nitrite by way of a nitrosuccinic acid intermediate.

Diazo compounds have two main Lewis structures in resonance: R2>C−–N+≡N and R2>CH=N+=N−
Diazo compounds have two main Lewis structures in resonance: R 2 >C − –N + ≡N and R 2 >CH=N + =N −
Solid state structure of the diazo compound t-BuO 2 CC(N 2 )C 6 H 4 NO 2 . Key distances: C-N = 1.329 Å, N-N = 1.121 Å. [ 12 ]