Pummerer rearrangement

The Pummerer rearrangement is an organic chemical reaction in which sulfoxides can be reacted with anhydrides . The products formed via various intermediate stages are α-acyloxysulfides, which can serve as synthetic equivalents to protected carbonyl compounds . The reaction was named after its discoverer Rudolf Pummerer (1882–1973).

The Pummerer rearrangement is also found as a side reaction of the Swern oxidation .

literature

Ottorino de Lucchi, Umberto Miotti, Giorgio Modena: The Pummerer Reaction of Sulfinyl Compounds . In: Organic Reactions . Vol. 40, 1991, pp. 157-184 , doi : 10.1002 / 0471264180.or040.03 .
Albert Padwa, David E. Gunn, Jr., Martin H. Osterhout: Application of the Pummerer Reaction Toward the Synthesis of Complex Carbocycles and Heterocycles . In: Synthesis . tape 1997 , no. December 12 , 1997, p. 1353-1377 , doi : 10.1055 / s-1997-1384 .

Albert Padwa, Scott K. Bur, Diana M. Danca, John D. Ginn, Stephen M. Lynch: Linked Pummerer-Mannich Ion Cyclizations for Heterocyclic Chemistry . In: Synlett . tape 2002 , no. 6 , June 2002, p. 851-862 , doi : 10.1055 / s-2002-31891 .

Individual evidence

↑ Rudolf Pummerer: About phenyl-sulfoxyacetic acid . In: Reports of the German Chemical Society . tape 42 , no. 2 (April – June), 1909, pp. 2282–2291 , doi : 10.1002 / cber.190904202126 .
^ Rudolf Pummerer: About phenylsulfoxy-acetic acid. (II.) . In: Reports of the German Chemical Society . tape 43 , no. 2 (April – October), 1910, pp. 1401-1412 , doi : 10.1002 / cber.19100430241 .

[1] Rudolf Pummerer: About phenyl-sulfoxyacetic acid . In: Reports of the German Chemical Society . tape 42 , no. 2 (April – June), 1909, pp. 2282–2291 , doi : 10.1002 / cber.190904202126 .

[2] Rudolf Pummerer: About phenylsulfoxy-acetic acid. (II.) . In: Reports of the German Chemical Society . tape 43 , no. 2 (April – October), 1910, pp. 1401-1412 , doi : 10.1002 / cber.19100430241 .