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Tin for Organic Synthesis, 7. New Regioselective Syntheses of Diaryl Sulfones, Arenesulfonamides, and Arenesulfonic Acid Sodium Salts
Author(s) -
Neumann Wilhelm P.,
Wicenec Christian
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260329
Subject(s) - chemistry , regioselectivity , reagent , intramolecular force , tin , alkyl , sodium , medicinal chemistry , sodium salt , group (periodic table) , chloride , leaving group , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , inorganic chemistry
The reaction of (trialkylstannyl)arenes 1 with corresponding reagents containing a chlorosulfonyl group leads, by exclusive ipso substitution, to important diaryl sulfones 2a – i , N 1‐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, N 1‐dialkylamidosulfonyl chloride/AlCl 3 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.