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| Authors | H. Cerfontain, B.H. Bakker, A. Koeberg-Telder, O. Wilmes | | Title | Relative Intramolecular Reactivity of the Insulated p Double Bond and the 14p Annulene Perimeter toward Sulfur Trioxide in the Sulfonation of Isopyrenes |
| Journal | LIEBIGS ANN-RECL |
| Volume | 1 |
| Year | 1997 |
| Pages | 49-53 |
| ISSN | 09473440 |
| Faculty | Faculty of Science |
| Institute/dept. | FNWI: Van 't Hoff Institute for Molecular Sciences (HIMS) |
| Keywords | annulenes; sulfur trioxide; sultones; carbyl sulfates; isopyrene |
| Classification | 35.51 |
| Abstract | 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 mol equiv. 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-l,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 potassium 16-hydroxy-7,14-dimethyl-l,6:8,13-ethanediylidene[14]annulene-15-sulfonate (4). |
| Document type | Article |
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