Oxidation for unsymmetrical bromo-1, 10-phenanthrolines and subsequent hydroxylation, decarbonylation and chlorination reactions. Issue 34 (23rd August 2018)

• Record Type: Journal Article
• Authors: Peng, Yu-Xin; Hu, Bin; Huang, Wei
• Is Part Of: Tetrahedron. Volume 74:Issue 34(2018)
• Page Start: 4495
• Page End: 4503
• Publication Date: 2018-08-23
• Subjects: Bromo-1, 10-phenanthroline -- Oxidation -- Hydroxylation -- Decarbonylation -- Chlorination; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.07.015
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A systematic investigation on the oxidation of unsymmetric bromo-phens is presented herein, where the reaction temperature is found to be the key parameter to generate oxidation or oxidation-bromination products. The regioselective C3-brominated compounds are produced in moderate yields in the cases of 2-bromo-phen and 4-bromo-phen. Subsequent hydroxylation and decarbonylation for bromo-phds are also studied, where a series of bromo-diazafluorenones and phen-triones have been isolated. Furthermore, various chlorination products have been obtained by treating bromo-phds or bromo-phts with excess POCl3 . Graphical abstract: