Carbon Cluster Compounds. Generation and Reorganization of the Homobullvalenyl Cation, an 11-Fold Degenerate Species

John Taylor Groves, King Way Ma

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18 Scopus citations

Abstract

Treatment of 4-bromo-4-trifluoroacetoxytetracyclo[4.3.2.02.9.03,5]undeca-7,10-diene (3) with sodium borohydride gave endo-4-hydroxytetracyclo[4.3.2.02,9.03,5]undeca-7,10-diene (5). Acetolysis of the corresponding triflate (9) proceeded at a rate virtually identical with those of the dihydro and tetrahydro derivatives 10 and 11. Solvolysis of the specifically deuter-ated triflate 9-d gave the alcohols 12 and 13 which were shown to have a statistical distribution of deuterium among the 11 skeletal carbons. This scrambling process has been interpreted in terms of multiple rearrangement paths of the intermediate homobullvalenyl and bicyclo[4.3.2]undecatetraenyl cations 1 and 2.

Original languageEnglish (US)
Pages (from-to)4076-4082
Number of pages7
JournalJournal of the American Chemical Society
Volume99
Issue number12
DOIs
StatePublished - Jan 1 1977

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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