Catalytic Racemization of Activated Organic Azides.

The first detailed description of the catalytic racemization of activated benzylic and allylic azides under mild conditions is reported. A kinetic analysis of the observed racemization indicates a first-order dependence on azide, a first-order dependence on catalyst, and that the rate of racemization correlates to σ+. A variety of azides with varying substitution patterns undergo facile racemization, and catalyst selection can tune this process.