REACTION OF TRICHLOROACETONITRILE WITH PRIMARY AND SECONDARY AMINES: PART III. STRUCTURE OF AMIDINIUM CATION IN THE LIGHT OF INFRARED STUDY

1959 ◽  
Vol 37 (8) ◽  
pp. 1260-1265 ◽  
Author(s):  
John C. Grivas ◽  
Alfred Taurins
Keyword(s):  
Nitrogen Atom ◽  
Infrared Spectra ◽  
Equilibrium Mixture ◽  
Secondary Amines ◽  
Infrared Study ◽  
Imino Nitrogen ◽  
Primary And Secondary Amines ◽  
Single Structure

The infrared spectra of 14 trichloro- and trifluoro-acetamidine hydrochlorides were studied. It was concluded that protonation occurs at the imino nitrogen atom of the N-substituted amidines. Both nitrogens of the amidine grouping, C(=N)N, become electron-deficient due to resonance leading to the single structure (III), regardless of which of the tautomers is present in the equilibrium mixture, and of the number and type of substituents on the amidine nitrogen atoms. These findings predestine to failure any attempts to isolate the two amidine tautomers, whenever amidinium salts are involved as intermediates.

REACTION OF TRICHLOROACETONITRILE WITH PRIMARY AND SECONDARY AMINES: PART II. INFRARED SPECTRA OF N-SUBSTITUTED TRICHLOROACETAMIDINES

1959 ◽  
Vol 37 (4) ◽  
pp. 795-802 ◽  
Author(s):  
John C. Grivas ◽  
Alfred Taurins
Keyword(s):  
Infrared Spectra ◽  
Secondary Amines ◽  
Amino Group ◽  
Polar Solvents ◽  
Primary And Secondary Amines ◽  
Secondary Amino ◽  
Solid Phases ◽  
Infrared Absorption Spectra ◽  
Degree Of Association ◽  
Liquid And Solid Phases

A correlation between the infrared absorption spectra and the structure of 13 N-mono- and N-di-substituted trichloroacetamidines is presented. N-Alkyl- and N-aryl-trichloroacetami-dines associate strongly in the liquid and solid phases, and exist only in the imino form in non-polar solvents. They can be characterized by a strong band (amidine II band) at 1510–1525 cm−1 and 1570–1580 cm−1 respectively which is attributed to the deformation vibration [Formula: see text] of the secondary amino group. The degree of association of N-substituted trichloroacetamidines changes in the following order of substitution:[Formula: see text]

Reaction of arylmethylenemalonaldehydes with some nucleophiles

1987 ◽  
Vol 52 (11) ◽  
pp. 2699-2709 ◽  
Author(s):  
Dalimil Dvořák ◽  
Zdeněk Arnold
Keyword(s):  
Inorganic Anions ◽  
Secondary Amines ◽  
Tertiary Amines ◽  
Primary And Secondary Amines ◽  
Dipolar Structure

Reaction of arylmethylenemalonaldehydes with tributylphosphine and tertiary amines affords compounds of dipolar structure whereas reaction with primary and secondary amines leads to 1,4-addition products. Salts of nucleophilic inorganic anions add to arylmethylenemalonaldehydes under formation of salts of substituted malonaldehydes.

Some 1-substitution derivatives of 4-aryl-2,3-dihalogeno-1-naphthols

1984 ◽  
Vol 49 (1) ◽  
pp. 110-121 ◽  
Author(s):  
Jiří Křepelka ◽  
Drahuše Vlčková ◽  
Milan Mělka
Keyword(s):  
Thionyl Chloride ◽  
Oxirane Ring ◽  
Secondary Amines ◽  
Two Phase ◽  
Lytic Effect ◽  
Primary And Secondary Amines ◽  
Phase Medium ◽  
Chloro Derivatives ◽  
Derivatives Of

Alkylation of derivatives of 4-aryl-1-naphthols (I-V) by 2,3-epoxypropyl chloride in methanolic sodium hydroxide gave epoxy derivatives VI, VIII, IX, XI and XII, apart from products of cleavage of the oxirane ring, VII and X. Analogous alkylation of compounds I, IV and V by 2-(N,N-diethylamino)ethyl chloride hydrochloride in a two-phase medium afforded basic ethers XIII to XV. The cleavage of the oxirane ring in compound VI by the action of primary and secondary amines, piperidine and substituted piperazines led to compounds XVI-XXIV. Reaction of thionyl chloride with compounds XXI, XXII and XXIV gave chloro derivatives XXV-XXVII.Exposure of compound XXII to 4-methylbenzenesulfonyl chloride produced compound XXVIII, retaining the secondary alcoholic group. In an antineoplastic screening in vivo none of the compounds prepared had an appreciable activity. Compound XVII, being an analogue of propranolol, was used in the test of isoproterenolic tachycardia, and showed a beta-lytic effect comparable with that of propranol.

ChemInform Abstract: Continuous-Flow Oxidative Cyanation of Primary and Secondary Amines Using Singlet Oxygen.

ChemInform ◽  
2014 ◽  
Vol 45 (30) ◽  
pp. no-no
Author(s):  
Dmitry B. Ushakov ◽  
Kerry Gilmore ◽  
Daniel Kopetzki ◽  
D. Tyler McQuade ◽  
Peter H. Seeberger
Keyword(s):  
Singlet Oxygen ◽  
Continuous Flow ◽  
Secondary Amines ◽  
Primary And Secondary Amines

Catalytic alkyl group exchange reaction of primary and secondary amines

1983 ◽  
Vol 105 (15) ◽  
pp. 5002-5011 ◽  
Author(s):  
Shunichi Murahashi ◽  
Noriaki Yoshimura ◽  
Tatsuo Tsumiyama ◽  
Takeyuki Kojima
Keyword(s):  
Exchange Reaction ◽  
Alkyl Group ◽  
Secondary Amines ◽  
Primary And Secondary Amines

Direct amidation of carboxylic acids with amines under microwave irradiation using silica gel as a solid support

2015 ◽  
Vol 17 (5) ◽  
pp. 3157-3163 ◽  
Author(s):  
Andrea Ojeda-Porras ◽  
Alejandra Hernández-Santana ◽  
Diego Gamba-Sánchez
Keyword(s):  
Fatty Acids ◽  
Microwave Irradiation ◽  
Carboxylic Acids ◽  
Silica Gel ◽  
Solid Support ◽  
Secondary Amines ◽  
Primary And Secondary Amines ◽  
Direct Amidation

A highly improved methodology for the direct amidation of carboxylic acids with amines using silica gel as a solid support and catalyst is described. Several examples using aliphatic, aromatic, unsaturated and fatty acids combined with primary and secondary amines are shown.

ChemInform Abstract: Palladium-Catalyzed Coupling of Functionalized Primary and Secondary Amines with Aryl and Heteroaryl Halides: Two Ligands Suffice in Most Cases.

ChemInform ◽  
2011 ◽  
Vol 42 (15) ◽  
pp. no-no
Author(s):  
Debabrata Maiti ◽  
Brett P. Fors ◽  
Jaclyn L. Henderson ◽  
Yoshinori Nakamura ◽  
Stephen L. Buchwald
Keyword(s):  
Secondary Amines ◽  
Primary And Secondary Amines ◽  
Palladium Catalyzed

Direct ring-opening of lactide with amines: application to the organo-catalyzed preparation of amide end-capped PLA and to the removal of residual lactide from PLA samples

2015 ◽  
Vol 6 (6) ◽  
pp. 989-997 ◽  
Author(s):  
Aurélie Alba ◽  
Olivier Thillaye du Boullay ◽  
Blanca Martin-Vaca ◽  
Didier Bourissou
Keyword(s):  
Ring Opening ◽  
Secondary Amines ◽  
Primary And Secondary Amines

Spontaneous ring-opening of lactide by primary and secondary amines has been applied to the preparation of well-defined amide end-capped PLA and to the removal of unreacted lactide from PLA samples.

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