酸催化下氧化偶氮苯類化合物重排為對羥基偶氮苯類化合物的反應。此反應與 Zinin聯苯胺重排只要較低濃度的酸催化不同,所需要的酸濃度較高(60-100%H2SO4)。有時候也可以得到鄰位羥基的異構體【Tetrahedron 1980, 36, 3177】
【Acc. Chem. Res.
1975, 8, 132】
p-Hydroxyazobenzene (2). Azoxybenzene
1 (198 mg, 1 mmol) was heated in H2SO4 (5 mL). The cooled mixture was diluted with water, purified via the sodium salt and recrystallized from MeOH,mp 152–153 ℃.【J Am Chem Soc.
1962, 84, 946】1 、See Yamamoto, J.; Nishigaki, Y.; Umezu, M.; Matsuura, T. Tetrahedron 1980, 36, 3177. 1034 See Buncel, E. Mech. Mol. Migr. 1968, 1, 61; Shine, H.J. Aromatic Rearrangements, Elsevier, NY, 2、1969,pp. 272–284, 357–359; Cox, R.A.; Buncel, E. in Patai, S. The Chemistry of the Hydrazo, Azo, and Azoxy Groups,pt. 2, Wiley, NY, 1975, pp. 808–837. 3、 See Shimao, I.; Oae, S. Bull. Chem. Soc. Jpn. 1983, 56, 643. 4、 Furin, G.G. Russ. Chem. Rev. 1987, 56, 532; Williams, D.L.H.; Buncel, E. Isot. Org. Chem. 1980, 5, 184;Buncel, E. Acc. Chem. Res. 1975, 8, 132. 5、 See Oae, S.; Fukumoto, T.; Yamagami, M. Bull. Chem. Soc. Jpn. 1963, 36, 601. 6、 Shemyakin, M.M.; Maimind, V.I.; Vaichunaite, B.K. Chem. Ind. (London) 1958, 755; Bull. Acad. Sci. USSRDiv. Chem. Sci. 1960, 808. Also see, Behr, L.C.; Hendley, E.C. J. Org. Chem. 1966, 31, 2715. 7、 See Cox, R.A. J. Am. Chem. Soc. 1974, 96, 1059. 8、 See Buncel, E.; Keum, S. J. Chem. Soc., Chem. Commun. 1983, 578. 9、Also see Shemyakin, M.M.; Agadzhanyan, Ts.E.; Maimind, V.I.; Kudryavtsev, R.V. Bull. Acad. Sci. USSRDiv. Chem. Sci. 1963, 1216; Hendley, E.C.; Duffey, D. J. Org. Chem. 1970, 35, 3579. 10、 See Cox, R.A.; Buncel, E. J. Am. Chem. Soc. 1975, 97, 1871. 11、 See Shimao, I.; Hashidzume, H. Bull. Chem. Soc. Jpn. 1976, 49, 754. 1044 See Shine, H.J.; Subotkowski, W.; Gruszecka, E. Can. J. Chem. 1986, 64, 1108.一、Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 509.二、March’s advanced organic chemistry : reactions, mechanisms, and structure. Eighth edition / Michael B Smith,P1436.