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Acylation of N-p-Toluenesulfonylpyrrole Under Friedel-Crafts Conditions. Evidence for Organoaluminu

Acylation of N-p-Toluenesulfonylpyrrole Under Friedel-Crafts Conditions. Evidence for Organoaluminu

  1. bluntshell
    Abstract
    The Friedel-Crafts acylation of N-p-toluenesulfonylpyrrole under Friedel-Crafts conditions has been
    reinvestigated. Evidence is presented in support of the hypothesis that when AlCl3 is used as the
    Lewis acid, acylation proceeds via reaction of an organoaluminum intermediate with the acyl halide.
    This leads to the production of the 3-acyl derivative as the major product. With weaker Lewis acids
    (EtAlCl2, Et2AlCl) or less than one equivalent of AlCl3 the relative amount of 2-acyl product is
    increased. A mechanistic rationalization is presented to explain these data.