Our own experimental studies have focussed on the reaction of p-nitrobenzenediazonium fluoroborate in DMF without catalysis.

The principal product was nitrobenzene. Decompositions in the prescence of added anisole, nitrobenzene, or iodobenzene gave product mixtures consistent with a p-nitrophenyl radical. The use of DMF, DMF-d1, DMF-d6 and DMF-d7 identified the sites of H-atom abstraction.

Experimental results (text version coming!)>
The exclusive production of 
nitrobenzene-4<I>d</I>1 when DMF-<I>d</I>7 was used establishes that DMF is the
sole source of hydrogens in this system.  The products from
DMF-<I>d</I>1 and DMF-<I>d</I>6 show the dominance of the protonated over 
the deuterated product.  While this might seem counterintuitive, 
<A HREF= it is consistent with a modest deuterium kinetic isotope effect in the H-atom abstraction reaction.

Introduction || Experimental || Theory || Conclusions || References

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Last updated 5/25/95