A Convenient “One-Pot” Reaction for Selective Monoalkylation of<i>N</i>,<i>N′</i>-Disubstituted Ethylenediamines

The alkali metal (Na + , K + , Rb + , Cs + ) bis-dithiocarbamate (bis-dtc) salts of N,N 0 -dibenzyl-1,2ethylenediamine have been prepared from the reaction of N,N 0 -dibenzyl-1,2-ethylenediamine with carbon disulfide in the presence of two equivalents of the corresponding alkali metal hydroxide. Additionally, the analogous triethylammonium derivative has been obtained. The resulting compounds have been analyzed as far as possible by elemental analysis, FAB + mass spectrometry, IR, UV-Vis and NMR ( 1 H, 13 C) spectroscopy, and single-crystal X-ray diffraction, showing that the composition of the metal salts can be described by the general formula. The solid-state and solution studies showed that all alkali metal ions participate in the formation of M-O and cation-p(arene) interactions, while M-S interactions are only observed for the larger alkali metals K + , Rb + and Cs + . As expected, within the alkali metal group there is a clear tendency for a decreasing number of M-O bonds in favor of M-S and cation-p(arene) interactions, however, only K + forms a semi-sandwich type complex with h 6 -coordination.

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“…N,N 0 -Dibenzy-1,2-lethylenediamine was synthesized as reported in the literature. 20 Compounds 1-4. General method.…”

Section: Synthesismentioning

confidence: 99%

Comparative analysis of M–O, M–S and cation–π(arene) interactions in the alkali metal (Na+, K+, Rb+, Cs+) bis-dithiocarbamate salts of N,N′-dibenzyl-1,2-ethylenediamine

et al. 2009

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“…As it arose from structural and physical features N-aryl-N'-benzyldihydroimidazolium salts (1n-u), belong to a new family of ionic liquids. 18 The physical data and elemental analyses of the new compounds are as follows: The method is operationally simple, with very low reaction times, easy work-up procedure and high reaction yields, also being the reagent a cheap commercially available chemical.…”

Section: Resultsmentioning

confidence: 99%

1,3-Dibromo-5,5-dimethylhydantoin as a New Imidazolidine Dehydrogenating Agent: Synthesis of 4,5-Dihydro-1H-imidazolium Salts

Salerno¹,

Caterina²,

Figueroa³

et al. 2006

HETEROCYCLES

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A study about the scope of the method for the attainment of 4,5-dihydro-1H-imidazolium salts by dehydrogenation of N,N´-dibenzyland N-aryl-N´-benzylimidazolidines is presented. Employed dehydrogenating agents were N-bromoacetamide (NBA), N-bromosuccinimide (NBS), carbon tetrachloride and 1,3-dibromo-5,5-dimethylhydantoin (DBDMH). DBDMH was the choice reagent due to the purity of the attained products, lowest reaction times and highest yields.

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“…[44][45][46][47][48] A two-step mechanism can be presented based on the Schiff base reaction for the preparation of N 1 ,N 2 -dibenzylethane-1,2-diamine (3). 49 The first step in the reaction is reversible, progressing through a carbinolamine intermediate and requires the removal of water, often by azeotropic distillation with benzene, to achieve high yields. The reaction is acid catalyzed, but catalysts are not generally required when aliphatic amines are involved.…”

Section: Chemical Synthesis Of N 1 N 2 -Dibenzylethane-12-diamine (3)-mentioning

confidence: 99%

An Efficient Electrochemical Method for the Synthesis of Quinoxaline-dione Derivatives from Oxidation of Catechols in the Presence ofN¹,N²-dibenzylethane-1,2-diamine

Dowlati

Nematollahi

Othman

2012

J. Electrochem. Soc.

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A series of 1,4-dibenzyl-1,2,3,4-tetrahydroquinoxaline-6,7-dione derivatives (6a-6c) were electrosynthesized. In the present work, electrochemical oxidation of catechols 1a-1d in the presence of the N1,N2-dibenzylethane-1,2-diamine (3) as a nucleophile, has been studied in aqueous solutions using cyclic voltammetry and controlled-potential coulometry (CPC) methods. Various parameters such as the applied potential, pH of the electrolytic solution, cell configuration and also purification techniques, were carried out to optimize the yields of corresponding products. New quinoxaline-6,7-dione derivatives were synthesized in excellent yield using an electrochemical procedure coupled with a Schiff base as a facile, efficient and practical method.

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A Convenient “One-Pot” Reaction for Selective Monoalkylation ofN,N′-Disubstituted Ethylenediamines

Cited by 17 publications

References 26 publications

Comparative analysis of M–O, M–S and cation–π(arene) interactions in the alkali metal (Na+, K+, Rb+, Cs+) bis-dithiocarbamate salts of N,N′-dibenzyl-1,2-ethylenediamine

Comparative analysis of M–O, M–S and cation–π(arene) interactions in the alkali metal (Na+, K+, Rb+, Cs+) bis-dithiocarbamate salts of N,N′-dibenzyl-1,2-ethylenediamine

1,3-Dibromo-5,5-dimethylhydantoin as a New Imidazolidine Dehydrogenating Agent: Synthesis of 4,5-Dihydro-1H-imidazolium Salts

An Efficient Electrochemical Method for the Synthesis of Quinoxaline-dione Derivatives from Oxidation of Catechols in the Presence ofN¹,N²-dibenzylethane-1,2-diamine

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A Convenient “One-Pot” Reaction for Selective Monoalkylation ofN,N′-Disubstituted Ethylenediamines

Cited by 17 publications

References 26 publications

Comparative analysis of M–O, M–S and cation–π(arene) interactions in the alkali metal (Na+, K+, Rb+, Cs+) bis-dithiocarbamate salts of N,N′-dibenzyl-1,2-ethylenediamine

Comparative analysis of M–O, M–S and cation–π(arene) interactions in the alkali metal (Na+, K+, Rb+, Cs+) bis-dithiocarbamate salts of N,N′-dibenzyl-1,2-ethylenediamine

1,3-Dibromo-5,5-dimethylhydantoin as a New Imidazolidine Dehydrogenating Agent: Synthesis of 4,5-Dihydro-1H-imidazolium Salts

An Efficient Electrochemical Method for the Synthesis of Quinoxaline-dione Derivatives from Oxidation of Catechols in the Presence ofN1,N2-dibenzylethane-1,2-diamine

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An Efficient Electrochemical Method for the Synthesis of Quinoxaline-dione Derivatives from Oxidation of Catechols in the Presence ofN¹,N²-dibenzylethane-1,2-diamine