Jie Jack Li 319 Hofmann rearrangement Upon treatment of primary amides with hypohalites, primary amines with one less carbon are obtained via the intermediacy of isocyanate Also know as the Hofmann degradation reaction isocyanate intermediate Example 1, An NBS variant2 Example 2, Iodosobenzene diacetate5 J.J Li, Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications, DOI 10.1007/978-3-319-03979-4_136, © Springer International Publishing Switzerland 2014 320 Name Reactions Example 3, Bromine and alkoxide6 Example 4, Sodium hypochlorite7 Example 5, The original conditions, bromine and hydroxide Example 6, Lead tetraacetate10 References Hofmann, A W Ber 1881, 14, 2725–2736 Jew, S.-s.; Kang, M.-h Arch Pharmacol Res 1994, 17, 490–491 Huang, X.; Seid, M.; Keillor, J W J Org Chem 1997, 62, 7495–7496 Togo, H.; Nabana, T.; Yamaguchi, K J Org Chem 2000, 65, 8391–8394 Yu, C.; Jiang, Y.; Liu, B.; Hu, L Tetrahedron Lett 2001, 42, 1449–1452 Jiang, X.; Wang, J.; Hu, J.; Ge, Z.; Hu, Y.; Hu, H.; Covey, D F Steroids 2001, 66, 655–662 Stick, R V.; Stubbs, K A J Carbohydr Chem 2005, 24, 529–547 Moriarty, R M J Org Chem 2005, 70, 28932903 (Review) El-Mariah, F.; Hosney, M.; Deeb, A Phosphorus, Sulfur Silicon Relat Elem 2006, 181, 2505–2517 10 Jia, Y.-M.; Liang, X.-M.; Chang, L.; Wang, D.-Q Synthesis 2007, 744–748 11 Gribble, G W Hofmann rearrangement In Name Reactions for Homologations-Part II; Li, J J., Ed.; Wiley: Hoboken, NJ, 2009, pp 164199 (Review) 12 Yoshimura, A.; Luedtke, M W.; Zhdankin, V V J Org Chem 2012, 77, 20872091 ... Example 5, The original conditions, bromine and hydroxide Example 6, Lead tetraacetate10 References Hofmann, A W Ber 1881, 14, 2725–2736 Jew, S.-s.; Kang, M.-h Arch Pharmacol Res 1994, 17, 490–491... 2505–2517 10 Jia, Y.-M.; Liang, X.-M.; Chang, L.; Wang, D.-Q Synthesis 2007, 744–748 11 Gribble, G W Hofmann rearrangement In Name Reactions for Homologations-Part II; Li, J J., Ed.; Wiley: Hoboken,