Diazene Fragmentations as Novel Alkane Syntheses

/3-Elimination (for the term see Section 4.1.1) of ortho-nitrobenzene sulfinic acid (F) leads from D to the N=N double bond of compound E. Because of the functional group C-N=N-H E is called a diazene. Diazenes assume a middle position between azo compounds, which contain a C-N=N-C group, and the NH compound diimide (sometimes called chi-mine H-N=N-H). 

Like diimide, diazenes are unstable at room temperature. They decompose while releasing elemental nitrogen. The decomposition mechanism is a radical chain reaction. 

Side Note 1.5. An (Almost) Universal C,C Bond-Forming Alkane Synthesis 

So radical intermediates can be accessed from full valence compounds. Keep electron transfer in mind when thinking about possible reaction mechanisms for a process. 

Motherwell, D. Crich, Free-Radical Chain Reactions in Organic Chemistry, Academic Press, San Diego, CA, 1991. 

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