Tunneling rearrangement of 1-azulenylcarbene.
J Am Chem Soc
; 134(32): 13204-7, 2012 Aug 15.
Article
em En
| MEDLINE
| ID: mdl-22799395
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.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2012
Tipo de documento:
Article