Substituted 1,10-Phenanthrolines. XIII. The Synthesis of New 4-Mono- and 4,7-Dialkyl- and -aryl-1,10-phenanthrolines¹

Abstract

The synthesis of the following 4-monosubstituted and 4,7-disubstituted 1,10-phenanthrolines is reported: -amyl, cyclohexyl, p-tolyl, p-ethylphenyl, p-i-butylphenyl, p-biphenylyl; also, 4,7-di-n-propyl, -di-n-tridecyl, and di-p-methoxyphenyl.

Octahedral Fe(II) and Ru(II) Complexes Based on a New Bis 1,10-Phenanthroline Ligand That Imposes a Well Defined Axis

“…Reduction of 3 with stannous chloride gave the amino derivative 4 in 95% yield. Compound 4 was finally reacted with 5 in o -phosphoric acid in the presence of arsenic pentaoxide to afford the desired phenanthroline 6 in 52% yield after recrystallization . Ligands L1 and L2 were prepared in a similar manner: deprotonation of 6 with a solution of LDA was followed by reaction with 0.5 equiv of either α,α‘-dibromo- p -xylene 7 or α,α‘-dibromo- m -xylene 8 .…”

Long-chain alkyl-substituted 1,10-phenanthrolines as surfactant ligands for transition-metal ions. 1. Synthesis of 4- and 4,7-undecyl-substituted 1,10-phenanthrolines

“…This was extracted with three 100-mL portions of diethyl ether which were then combined, washed with 5 % sodium bicarbonate solution, then with saturated brine, and dried over anhydrous magnesium sulfate. Removal of the solvent at reduced pressure yielded 38.2 g (90.0% yield) of crude 1-tetradecen-3-ol: NMR (60 MHz, CDCI3) 5.8 (m, 1 H), 5.25 (d, J = 5 Hz, 1 ), 5.0 (m, 1 ), 4.08 (d, J = 3 Hz, 1 H), 2.65 (br s, 1 ), 1.25 (s, 20 ), 0.90 (t, J = 2.5 Hz, 3 H); IR (neat on NaCI) 3350s, 3080w, 2920s, 2850s, 1640w, 1465s, 1375w, 1055w, 985s, 915s, 715w cm"1.…”

“…The synthesis of substituted 1,1 O-phenanthrolines has, in the majority of cases, been accomplished by methods involving modifications of the Skraup reaction (2)(3)(4)(5)(6)(7)(8)(9) or the Conrad-LImpach synthesis (8,9).…”