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 language | English |
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Pages (from-to) | 8244-8246 |
Number of pages | 3 |
Journal | Journal of the American Chemical Society |
Volume | 100 |
Issue number | 26 |
DOIs | |
Publication status | Published - 1978 |
Externally published | Yes |
ASJC Scopus subject areas
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry