REVERSIBILITY IN THE SULFONATION OF 3,5-DIMETHOXYPHENOL AND ITS METHANESULFONATE ESTER

References

• Aromatic sulfonation part 112. For part 111, see ref. 4.
   Google Scholar
• For reasons of convenience, the sulfonic acid products have all been numbered as for the starting substrate, except for 4
   Google Scholar
• Cerfontain , H. , Koeberg-Telder , A. , Lambrechts , H. J. A. and de Wit , P. 1984 . J. Org. Chem. , 49 : 4917
   Web of Science ®Google Scholar
• Cerfontain , H. , Ansink , H. R. W. , Coenjaarts , N. J. , de Graaf , E. J. and Koeberg-Telder , A. 1989 . Red. Trav. Chim. Pays-Bas , 108 : 445
   Google Scholar
• This type of cyclic sulfonate sulfate anhydride is known to hydrolyse under aqueous conditions to afford the corresponding phenolsulfonic acid quantitatively.6
   Google Scholar
• Cerfontain , H. , Coenjaarts , N. J. and Koeberg-Telder , A. 1989 . Red. Trav. Chim. Pays-Bas , 108 : 7
   Google Scholar
• Note that the ratio 1-2-S:1-4-S is the same as after aqueous work-up!
   Google Scholar
• Bakker , B. H. and Cerfontain , H. 1989 . Tetrahedron Lett. , : 5451
   Google Scholar
• It has been outlined that the proton abstraction from sulfonation σ-complexes which lead to overcrowded arenesulfonic acid products is the rate-limiting step.10
   Google Scholar
• Lammertsma , K. and Cerfontain , H. 1980 . J. Chem. Soc. Perkin Trans. , 2 : 28
   Google Scholar
• Cerfontain , H. 1985 . Red. Trav. Chim. Pays-Bas , 104 : 153
   Google Scholar
• Vogel , A. 1970 . “Practical Organic Chemistry,” , 3rd Ed. , 684 London : Longmans, Green and Co. Ltd. .
   Google Scholar