Schmidt Reaction

Mechanism of the Schmidt Reaction

Original publication	Ber. Dtsch. Chem. Ges.. 1924, 57, 704. J. Am. Chem. Soc.. 1951, 73, 3087.
Reviews	Chem. Heterocycl. Compd.. 1975, 11, 626. Org. React.. 1946, 3, 307. Org. React.. 2012, 78, 1. Russ. Chem. Rev.. 1971, 40, 835. Russ. Chem. Rev.. 1978, 47, 1084.

Sample reactions

NaN3

PPA

120 °C, 30 min, 63%

"Also isolated was 13 % of the enamine regioisomer."

TfOH

CH2Cl2

0 °C, 6 h, 79%

H2SO4, NaN3

CF3CO2H

45-50 °C, 5 h, 35%