Homologation of n-alkanes on tungsten films. A novel, highly selective reaction of intermediate carbenes

Authors:
  • COCormac O'DOnohoe
    Cormac O'DOnohoe
  • JCJohn K. A. Clarke
    John K. A. Clarke
  • JRJohn J. Rooney
    John J. Rooney
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Abstract
The n-alkanes (C5) undergo a novel remarkably selective reaction in high yield whereby they are singly and multiply homologated to the higher n-paraffins during hydrogenolysis on tungsten films; the reaction, which also occurs on several other metal catalysts but there affords aromatic products at the higher temperatures employed, is discussed in terms of intermediate α-olefins and surface methylenes adding to each other in a highly selective fashion giving metallocyclobutanes, which in turn are hydrogenated to the homologous paraffin, or isomerize to new α-olefins with repetitive chain growth.