ISSN:
0009-2940
Keywords:
Aromatic substitution, electrophilic
;
Sulfones, synthesis of
;
Sulfonamides, synthesis of
;
Sulfonic acids, sodium salts, synthesis of
;
Stannanes, trialkylaryl-, application of
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The reaction of (trialkylstannyl)arenes 1 with corresponding reagents containing a chlorosulfonyl group leads, by exclusive ipso substitution, to important diaryl sulfones 2a - i, N1-alkyl-arenesulfonamides 8a - f, and sodium arenesulfonates 13a - c in high yields under mild conditions. The specific leaving ability of the stannyl group allows, moreover, the preparation of arylsulfonyl isomers which are not accessible under the influence of the conventional directing forces of substituents. With N, N1-dialkylamidosulfonyl chloride/AlCl3 complexes no destannylation takes place, but the first intramolecular sulfonyltin complex 11 is formed. This result is used to discuss details of the mechanism involved.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260329
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