Tunneling rearrangement of 1-azulenylcarbene

J Am Chem Soc. 2012 Aug 15;134(32):13204-7. doi: 10.1021/ja3050376. Epub 2012 Jul 31.

Abstract

1-Azulenylcarbene was synthesized by photolysis of 1-azulenyldiazomethane in argon or neon matrices at 3-10 K. The highly polar singlet carbene is only metastable and undergoes a tunneling rearrangement to 8-methylene-bicyclo[5.3.0]deca-1,3,5,6,9-pentaene. After substitution of the 4 and 8 positions with deuterium, the rearrangement is completely inhibited. This indicates a very large kinetic isotope effect, as expected for a tunneling reaction.