Oxidation of Tertiary Homoallylic Alcohols by Thallium Trinitrate: Fragmentation vs. Ring Contraction

نویسندگان

  • Luiz F. Silva
  • Samir A. P. Quintiliano
  • Helena M. C. Ferraz
  • Leonardo S. Santos
  • Marcos N. Eberlin
چکیده

A oxidação de álcoois homoalílicos terciários com trinitrato de tálio (TTN) foi investigada. Os álcoois que possuem uma metila na posição alílica perdem uma molécula de acetona via uma reação de fragmentação, levando a uma mistura de álcoois alílicos isoméricos como principais produtos, juntamente com os correspondentes derivados acetilados. Por outro lado, o tratamento com TTN de álcoois terciários análogos, sem a metila na posição alílica, fornece indanos, através de uma reação de contração de anel.

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تاریخ انتشار 2006