Pschorr Reaction

R. Pschorr, Ber. 29, 496 (1896).

Synthesis of phenanthrene derivatives from diazotized α-aryl-o-aminocinnamic acids by intramolecular arylation:



Reviews: P. H. Leake, Chem. Rev. 56, 27 (1956); D. F. De Tar, Org. React. 9, 409 (1957); R. A. Abramovitch, Advan. Free Rad. Chem. 2, 88 (1967); T. Kametani, K. Fukumoto, J. Heterocyclic Chem. 8, 341 (1971); S. Foldeak, Tetrahedron 27, 3465 (1971); T. S. Kametani et al., ibid. 27, 5367 (1971); F. F. Gadallah et al., J. Org. Chem. 38, 2386 (1973); S. M. Kupchan et al., ibid. 405; G. Daidone et al., J. Heterocyclic Chem. 17, 1409 (1980). Mechanistic study: P. Hanson et al., J. Chem. Soc. Perkin Trans II 1999, 49. Cf. Gomberg-Bachman Reaction; Meerwein Arylation.