Spiroaromaticity in Spiro[2.3]hexadienyl Anions. Kinetic Acidities in Highly Basic Media

M. F. Semmelhack, R. J. DeFranco, Z. Margolin, J. Stock

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Experimental tests for special stabilization (spiroaromaticity) in a spiro[2.3]hexadienyl anion compared with a series of spiro[2.3]hex-4-en-6-yl anions using polarography and kinetic acidity measurements reveal no significant stabilization. The kinetic acidity data were obtained by hydroxide ion catalyzed tritium exchange in dimethyl sulfoxide-water mixtures. The second-order rate constants were determined to be as follows: for 12,4.6 10-5; for 13, 24.14 × 10-5; for 14, 2.03 × 10-5; for 15 (mixture of isomers), 5.70 × 10-5. Brpnsted coefficients (3) of ca. 0.80 for proton abstraction from the spiro[2.3]hexadiene 12 and spiro[2.3]hex-4-ene 13 suggest that the transition states from both compounds resemble the carbanionic products.

Original languageEnglish (US)
Pages (from-to)426-432
Number of pages7
JournalJournal of the American Chemical Society
Issue number2
StatePublished - Jan 1 1973
Externally publishedYes

All Science Journal Classification (ASJC) codes

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


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