Dipole Moments, Configuration, and Conformation of Tricyclo[5.1.0.03,5]octane Derivatives and Related Compounds

W. D. Kumler, Robert Boikess, P. Bruck, S. Winstein

Research output: Contribution to journalArticle

31 Scopus citations

Abstract

Tricyclo[5.1.0.03-5]octane (VI), 4,4-dibromotricyclo[5.1.0.03-5]octane (Y), and 4,4,8,8-tetrabromotricyclo-[5.1.0.03-5]octane (III) have been prepared. The dipole moments of these compounds as well as those of norcarane (VIII), Δ3-norcarene (IV), 7,7-dibromobicyclo[4.1.0]heptane (VII), Δ3-7,7-dibromobicyclo [4.1.0] heptene (II), 1,4-eyclohexadiene (I), cyclohexene, and cyclopentene have been measured. Zero dipole moment for III proves its configuration is trans and the six-membered ring has a relatively flat conformation. The methods of preparation indicate a trans configuration for VI and Y and the dipole moment values favor nearly flat conformations for the six-membered rings in these compounds. Cyclohexene and cyclopentene were found to have dipole moments of 0.21 D. which are considerably smaller than most values in the literature. Norcarane has a moment of 0,44 D. The evidence indicates the central ring is relatively flat when either cyclopropane or olefinic groups are on opposite sides of a six-membered ring.

Original languageEnglish (US)
Pages (from-to)3126-3130
Number of pages5
JournalJournal of the American Chemical Society
Volume86
Issue number15
DOIs
StatePublished - Aug 1 1964
Externally publishedYes

All Science Journal Classification (ASJC) codes

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

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