Clean-Chemistry Sulfonation of Aromatics

2002 ◽  
Vol 2002 (7) ◽  
pp. 326-327 ◽  
Author(s):  
Brian W. Corby ◽  
Anthony D. Gray ◽  
Padraig J. Meaney ◽  
Michael J. Falvey ◽  
Gregory P. Lawrence ◽  
...  

A solution of TFAA/H2SO4 is an atom-efficient liquid-phase system for rapid sulfonation of aromatic structures; H2SO4 is consumed stoichiometrically and the spent trifluoroacetic anhydride (TFAA) is readily recovered as trifluoroacetic acid (TFA) which can be recycled to TFAA.

ChemInform ◽  
2015 ◽  
Vol 46 (17) ◽  
pp. no-no
Author(s):  
Yueer Yan ◽  
Xiao Guo ◽  
Yahong Zhang ◽  
Yi Tang

1993 ◽  
Vol 25 (5) ◽  
pp. 363-374
Author(s):  
Matae Iwasaki ◽  
Tetsuo Sakka ◽  
Shigeyuki Ohashi ◽  
Yoshikazu Miyake ◽  
Hiroshi Matsushita

1998 ◽  
Vol 16 (1) ◽  
pp. 27-44 ◽  
Author(s):  
S. D. Doig ◽  
A. T. Boam ◽  
D. J. Leak ◽  
A. G. Livingston ◽  
D. C. Stuckey

2016 ◽  
Vol 69 (1) ◽  
pp. 61 ◽  
Author(s):  
Rebecca E. Norman ◽  
Michael V. Perkins ◽  
Andris J. Liepa ◽  
Craig L. Francis

Treatment of pyrazolo[1,5-b][1,2,4,6]thiatriazines 1 with the Vilsmeier–Haack reagent afforded pyrazolo[1,5-a][1,3,5]triazines 5. Reaction of compounds 1 with trifluoroacetic anhydride, dimethyl sulfoxide, and triethylamine afforded 5-dimethylsulfanylidene derivatives 8. The guanidino-pyrazole-sulfonic acid 9 was produced from treatment of compounds 1 with trifluoroacetic acid under anhydrous conditions. Similar treatment in the presence of water afforded the desulfonated pyrazolo-guanidine 6. Reactions of 6 with one-carbon electrophiles provided various 4-substituted pyrazolo[1,5-a][1,3,5]triazines 5. Attempted catalytic hydrogenolysis of N7-benzyl pyrazolo[1,5-b][1,2,4,6]thiatriazines 2 in alcohols led to sulfamates 12 from thiatriazine ring cleavage. Ethyl acetate or tert-butanol as solvent allowed successful debenzylation to provide compounds 1. Aminolysis of compounds 2 gave sulfamides 13. Thermal rearrangement of compounds 2 afforded 6-benzyl-pyrazolo[3,4-e][1,2,4]thiadiazines 14.


2013 ◽  
Vol 89 (4) ◽  
pp. 522-527 ◽  
Author(s):  
Michiaki Matsumoto ◽  
Takashi Sugimoto ◽  
Yudai Ishiguro ◽  
Hiroyuki Yamaguchi ◽  
Kazuo Kondo

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