Synthesis of 2,9-Dichloro-1,10-phenanthroline from N,N′-Annelated Phenanthrolinediones

Abstract

Though the chlorination of an N,N′-annelated phenanthrolinedione, 3,6,7,9-tetrahydro-5H-[1,4]diazepino[1,2,3,4-lmn][1,10]phenanthroline-3,9-dione, gave 2,9-dichloro-1,10-phenanthroline, another dione, 3,5,6,8-tetrahydropyrazino[1,2,3,4-lmn][1,10]phenanthroline-3,8-dione, did not. It demonstrated a simultanous introduction of two chlorine substituents to non-substituted 1,10-phenanthroline via only the former intermediate.

Synthesis of a Bis‐macrocycle Containing Two Back‐to‐Back Rigidly Connected 1,10‐Phenanthroline Units as a Central Core and its Incorporation in a Handcuff‐Like Catenane

“…The a-dione 5 was prepared according to a literature procedure [10] by oxidising 4 with KBr and HNO 3 in concentrated sulfuric acid. After work-up and column chromatography, 5 was obtained as a yellow solid.…”

Biphasic Synthesis of Hydrogen Peroxide from Carbon Monoxide, Water, and Oxygen Catalyzed by Palladium Complexes with Bidentate Nitrogen Ligands

“…[14,15] General procedure for the synthesis of hydrogen peroxide: Pd(OAc) 2 (0.07 mmol), CF 3 COOH or C 7 F 15 COOH (2.8 mmol), and one of the ligands 1 ± 8 (0.28 mmol) were dissolved in a mixture of 1,2,4-trichlorobenzene (40 mL) and 2-methyl-2-butanol (60 mL), and stirred for 6 h at 25 8C. The resulting solution was added to water (80 mL) to form a biphasic system and poured into an autoclave containing a glass liner.…”

Catalytic Conversions in Water. Part 23: Steric Effects and Increased Substrate Scope in the Palladium‐Neocuproine Catalyzed Aerobic Oxidation of Alcohols in Aqueous Solvents#

“…2,9-Bis(trifluoromethyl)-1,10-phenanthroline (5), [25] 2,9-di-nbutyl-1,10-phenanthroline (6), [36] 2-Methyl-1,10-phenanthroline (9), [37] 2,9-dichloro-1,10-phenanthroline (16), [38] 2-phenyl-1,10-phenanthroline (17), [39] 2,9-bis(trichloromethyl)-1,10-phenanthroline (19), [40] were prepared according to literature procedures. Previously unreported data are given below.…”