Arndt-Eistert Synthesis

• General Characteristics

The Wolff rearrangement of diazoketones prepared from acid chlorides and diazomethane is especially called the Arndt-Estert synthesis, which is an effective way of one-carbon homologation of carboxylic acids.

The use of less explosive trimethylsilyldiazomethane is recommended for better experimental safety.

• General References

・Eistert, B.; Arndt, F. Chem Ber. 1927, 60, 1364.
・Arndt, F.; Eistert, B. Ber. 1935, 68, 200. doi:10.1002/cber.19350680142
・Bachmann, W. E.; Struve, W. S. Org. React. 1942, 1, 38.
・Meier, H. et al. Angew. Chem. Int. Ed. Engl. 1975, 14, 32.
・Aoyama, T.; Shiori, T. Chem. Pharm. Bull. 1981, 29, 3248.
・Smith, A. B., III et al. J. Am. Chem. Soc. 1986, 108, 3110. DOI: 10.1021/ja00271a054
・Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. DOI:10.1021/cr00028a010
・Cesar, J.; Dolenc, M. S. Tetrahedron Lett. 2001, 42, 7099. doi:10.1016/S0040-4039(01)01458-7

• Reaction Mechanism

Same as the Wolff rearrangement. Ref: J. Am. Chem. Soc.1942, 64, 3043.

• Examples

• Experimental Procedure

• Experimental Tips

• References

• Related Books

homologation of carboxylic acid, rearrangemtn of diazoketones, wolff rearrangement