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Rearrangement of aromatic sulfonate anions in the gas phase

✍ Scribed by Roger W. Binkley; Thomas W. Flechtner; Michael J. S. Tevesz; Witold Winnik; Boyu Zhong

Publisher: John Wiley and Sons
Year: 1993
Tongue: English
Weight: 319 KB
Volume: 28
Category: Article
ISSN: 1076-5174
DOI: 10.1002/oms.1210280708

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✦ Synopsis

Collisionally activated dissociation of deprotonated aromatic sulfonic acids in the gas phase causes rearrangement and fragmentation to produce the corresponding phenoxide ions. The mechanism for this reaction has been investigated and the results of this study favor initial intramolecular nucleophilic addition of a sulfonate oxygen atom to the aromatic ring, a process which is followed by heterolytic cleavage of the carbonsulfur bond to rearomatize the ring. The product from this addition4imination sequence is the anion of a sulfurous acid halfester, which loses SO, to generate the corresponding phenoxide ion.

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