Aromatic Sulfonation. 67.1 Sulfonation of the 1,6-Methano[10]annulene System. Evidence for Ipso Attack with the 2,7-Dimethyl Derivative

Koop Lammertsma, Hans Cerfontain

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

Sulfonation of 1,6-methano[ 10]annulene (1) with 0.9 equiv of SO3 in dioxane yields exclusively the 2-sulfonic acid, and with 4 equiv of SO3 only the 2,7-disulfonic acid. The primary kinetic isotope effect for the monosulfonation of 1 was determined to be KH/KD=3.8 ± 0.3. Sulfonation of 2-methyl-l yielded the 5-sulfonic acid. The reaction of 2,7-dimethyl-1 with SO3 in dioxane resulted in peri (65%) and ipso (35%) substitution, with formation of 2,7-dimethyl-l-5-sulfonic acid and 2-methyl-1-7-sulfonic acid, respectively.

Original languageEnglish
Pages (from-to)8244-8246
Number of pages3
JournalJournal of the American Chemical Society
Volume100
Issue number26
DOIs
Publication statusPublished - 1978
Externally publishedYes

ASJC Scopus subject areas

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

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