Spiro[4.4]nonatetraene and spiro[4.4]nona-1,3,7-triene. Synthesis and properties. Effects of spiroconjugation

M. F. Semmelhack, J. S. Foos, S. Katz

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Spiro[4.4]nonatetraene (1) was prepared for the first time by a relatively direct synthesis starting from allyl bromide and diethyl malonate. Spiro[4.4]nona-l,3,7-triene (2) was obtained by a new route, starting from cyclopentadienide anion and 4,5-di(bromomethyl)-2,2-dimethyl-l,3-dioxolane (16). Comparison of the spectral and chemical properties of 1, 2, and spiro[4.4]nona-l,3-diene (10) revealed significant effects of spiroconjugation. The uv spectrum of 1 showed a red shift of 22 nm and lowered extinction coefficient compared to 2 and 10, com-pletely consistent with earlier theoretical predictions.

Original languageEnglish (US)
Pages (from-to)7325-7336
Number of pages12
JournalJournal of the American Chemical Society
Issue number22
StatePublished - Oct 1 1973
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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