Haller-Bauer Reaction

A. Haller, E. Bauer, Compt. Rend. 148, 70, 127 (1909); 149, 5 (1909).

Cleavage of non-enolizable ketones with sodium amide; frequently applied to formation of trisubstituted acetic acid:



K. E. Hamlin, A. W. Weston, Org. React. 9, 1 (1957); H. M. Walborsky et al., J. Org. Chem. 36, 2937 (1971); E. M. Kaiser, C. O. Warner, Synthesis 1975, 395. Applications: G. Mehta, M. Praveen, J. Org. Chem. 60, 279 (1995); idem et al., Tetrahedron Letters 37, 2289 (1996); A. Mittra et al., J. Org. Chem. 63, 9555 (1998). Reviews and extension to amide formation: J. P. Gilday, L. A. Paquette, Org. Prep. Proced. Int. 22, 167-201 (1990); G. Mahta, R. V. Venkateswaran, Tetrahedron 56, 1399 (2000).