Tin for organic synthesis. 10. Unconventional regiospecific syntheses of aromatic carbonamides and thiocarbonamides by means of tin-mediated Friedel-Crafts …
M Arnswald, WP Neumann
Index: Arnswald, Martin; Neumann, Wilhelm P. Journal of Organic Chemistry, 1993 , vol. 58, # 25 p. 7022 - 7028
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Citation Number: 34
Abstract
Friedel-Crafta reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N- tosylcarbonamides 3 via ipso substitution of the stannyl group. Thus, unconventionally substituted aromatic carbonamides can be obtained. The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N- (arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on ...
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