Zinin联苯胺重排

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酸催化下氢化偶氮苯重排得到4,4-二氨基联苯 (benzidine)和2,4-二氨基联苯的反应。


反应机理



反应实例

Org. Lett2006, 8, 4919-4922



Org. Lett2007, 9, 3185-3186



EtOH (2 mL) and five drops conc HCl were added to 6 (100 mg, 0.21 mmol), at r.t.The mixture was refluxed for 2 h, cooled to 0 ℃, neutralized with solid NaHCO3, filtered, and concentrated in vacuo. To the residue were added MeCN (2 mL), AcCl (0.08 mL, 5 equiv) and NaOAc(94 mg, 5 equiv). After 12 h, aq workup and chromatography afforded 44 mg of (46%).

Org. Lett2007, 9, 3185-3186




参考文献


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8. Benniston, A. C.; Clegg, W.; Harriman, A.; Harrington, R. W.; Li, P.; Sams, C. Tetrahedron Lett2003, 44, 2665-2667. 

9. Hong, W.-X.; Chen, L.-J.; Zhong, C.-L.; Yao, Z.-J. Org. Lett2006, 8, 4919-4922. 

10. Kim, H.-Y.; Lee, W.-J.; Kang, H.-M.; Cho, C.-G. Org. Lett2007, 9, 3185-3186. 

11. De, C. K.; Pesciaioli, F.; List, B. Angew. Chem. Int. Ed. 2013, 52, 9293–9295.


编译自Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Zinin benzidine (semidne) rearrangement,page 659-660.



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