ISSN:
0947-3440
Keywords:
Sulfur trioxide sulfonation
;
[14]Annulene
;
[14]Annulenemono- and -disulfonic acids
;
β-Sultone and carbyl sulfate (pyrosultone) formation
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The sulfonation of isopyrene (1) and its 5-methyl- and 5,10-dimethyl derivative 2 and 3 with SO3 in both dichloromethane and nitromethane as solvent has been studied. Reaction of 1 and 2 leads to sulfodehydrogenation in which SO3 reacts as a monodentate electrophile, the initial products being 1-5-sulfonic acid (1-5-S) and 2-10-S, respectively. In the presence of a sufficiently large amount of SO3 1-5-S is subsequently converted into 1-5,10-S2. With 3, using 2.0 molequiv, of the sulfonating reagent in dichloromethane, the SO3 adds as a bidentate electrophile to the “central C=C bond” with formation of 7,14-dimethyl-1,6:8,13-ethanediylidene-[14]annulene-15,16-sultone (5) and the corresponding pyrosultone 6. Upon subsequent hydrolysis and neutralization with aqueous KOH the eventually obtained product is potasium 16-hydroxy-7,14-dimethyl-1,6:8,13-ethanediylidene-[14]annulene-15-sulfonate (4).
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970110
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