Arndt-Eistert Synthesis

F. Arndt, B. Eistert, Ber. 68, 200 (1935).

Homologation of carboxylic acids:



Alternative reagent for diazomethane: T. Aoyama, Tetrahedron Letters 21, 4461 (1980). Application to synthesis of unsaturated diazoketones: T. Hudlicky et al., ibid. 1979, 2667; K. Gademann et al., Angew. Chem. Int. Ed. 38, 1223 (1999); via ultrasonic activation: J-Y. Winum et al., Tetrahedron Letters 37, 1781 (1996); of amino acids: R. E. Marti et al., ibid. 38, 6145 (1997); R. J. DeVita et al., Bioorg. Med. Chem. Letters 9, 2621 (1999). Reviews: W. E. Bachmann, W. S. Struve, Org. React. 1, 38-62 (1942); B. Eistert in Newer Methods in Preparative Organic Chemistry vol. 1 (Interscience, New York, 1948) pp 513-570; G. B. Gill, Comp. Org. Syn. 3, 888-889 (1991). Cf. Wolff Rearrangement.