STUDIES IN URETHANES: V. NEW ACYL DI-URETHANES AND THEIR REACTIONS WITH AMMONIA AND AMINES

1931 ◽  
Vol 4 (4) ◽  
pp. 361-371
Author(s):  
Steward Basterfield ◽  
C. Vernon Wilson ◽  
Margaret E. Greig
Keyword(s):  
Ionization Constant ◽  
Acid Amide ◽  
Primary Amines ◽  
Acyl Radical ◽  
Amide Formation

Previous studies have shown that oxalyl-, malonyl- and phthalyldi-urethanes are decomposed readily by ammonia and primary amines with the loss of one or both urethane groups and the production of the amides of the dibasic acids, or of urethane-amides, and ureido-amides. Acyldi-ureas were not formed as might have been expected.The present study deals mainly with the preparation and properties of succinyl-, glutaryl-, and adipyldi-urethanes. While with ammonia and ethylamine these yield amides, with aniline they give the acyldi-(phenylureas), which are decomposed by further action of the base into acylanilides, and diphenylurea. The mode of decomposition is strongly influenced by the nature of the acyl radical as well as that of the reacting base. The results may be provisionally generalized in the statement that, with a given base, the tendency of a di-urethane to yield the acid amide is more pronounced the stronger the acid from which the radical is derived, while with a given di-urethane the tendency to amide formation is more pronounced the stronger the reacting base. The formation of acyldi-ureas becomes evident when the di-urethane contains the radical of an acid with an ionization constant of the order of 10−6 or less.

STUDIES IN URETHANES: VII REACTIONS OF ACYL DIURETHANES WITH AMMONIA AND PRIMARY AMINES. STABILIZING EFFECT OF THE PHENYL RADICAL IN PHENYLMALONYL- AND PHENYLSUCCINYL-DIURETHANE

1942 ◽  
Vol 20b (11) ◽  
pp. 240-245
Author(s):  
S. Basterfield ◽  
A. J. Dyck
Keyword(s):  
Oxalic Acid ◽  
Primary Amines ◽  
Phenyl Radical ◽  
Acyl Radical ◽  
Definite Evidence ◽  
Rapid Decomposition ◽  
Mechanism Of Decomposition ◽  
Stabilizing Effect ◽  
The One

In previous studies it has been shown that the mechanism of decomposition of acyl diurethanes by ammonia and amines is correlated to some extent with the strength of the acid from which the acyl radical is derived and of the base used as ammonolytic reagent. In the oxalic acid series a diurea was obtained from succinyl-diurethane and aniline, but not from oxalyl- or malonyl-diurethane. Succinyl-diurethane gave no diurea with stronger bases.It is shown in the present study that phenylmalonyl-diurethane yields with aniline a diurea which undergoes rapid decomposition on being heated with aniline at 150 °C. Phenylsuccinyl-diurethane gives with aniline a diurea that is much more stable than the one obtained from succinyl-diurethane, as judged by the rate of decomposition on heating with aniline at 150°. No definite evidence of diurea formation was obtained with bases stronger than aniline.

scholarly journals Studies and Synthesis of Substituted 4-Biphenyl Acetamide Derivatives

2019 ◽  
Vol 31 (3) ◽  
pp. 510-514
Author(s):  
Anju Khullar
Keyword(s):  
Acetic Acid ◽  
Thionyl Chloride ◽  
Spectral Methods ◽  
Aromatic Amines ◽  
Acetyl Chloride ◽  
Acid Amide ◽  
Primary Amines ◽  
Curvularia Lunata ◽  
Fusarium Udum ◽  
Amide Derivatives

A new series of substituted 4-biphenylamides have been synthesized by condensation of 4-biphenyl acetic acid with different primary amines (aromatic and aliphatic). 4-Biphenyl acetic acid was first treated with thionyl chloride in dry benzene to prepare substituted 4-biphenyl acetyl chloride, which is then treated with different aliphatic or aromatic amines to synthesize various substituted 4-biphenyl acid-amide derivatives. The structure of newly synthesized compounds has been established by analytical and spectral methods. These synthesized compounds have shown antifungal properties against Fusarium udum and Curvularia lunata.

Dielectric study of primary amines from room temperature down to −180 °C and from 10 kHz up to 35 GHz

1999 ◽  
Vol 8 (3) ◽  
pp. 241-246
Author(s):  
J. M. Forniés-Marquina ◽  
A. Siblini ◽  
L. Jorat ◽  
G. Noyel
Keyword(s):  
Room Temperature ◽  
Primary Amines ◽  
Dielectric Study

Acyl Radical Macrocyclisations. A Synthesis of the Furanocembrane Unit in Lophotoxin and Pukalide

Synlett ◽  
1991 ◽  
Vol 1991 (04) ◽  
pp. 335-336 ◽  
Author(s):  
Martin P. Astley ◽  
Gerald Pattenden
Keyword(s):  
Acyl Radical

Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage–Independent Activation of Strong C–O Bonds

2018 ◽  
Author(s):  
Erin Stache ◽  
Alyssa B. Ertel ◽  
Tomislav Rovis ◽  
Abigail G. Doyle
Keyword(s):  
Carboxylic Acids ◽  
Functional Groups ◽  
Single Step ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Acyl Radical ◽  
Synthetic Strategy ◽  
Acyl Radicals ◽  
Benzyl Radicals ◽  
Aliphatic Carboxylic Acids

Alcohols and carboxylic acids are ubiquitous functional groups found in organic molecules that could serve as radical precursors, but C–O bonds remain difficult to activate. We report a synthetic strategy for direct access to both alkyl and acyl radicals from these ubiquitous functional groups via photoredox catalysis. This method exploits the unique reactivity of phosphoranyl radicals, generated from a polar/SET crossover between a phosphine radical cation and an oxygen centered nucleophile. We first show the desired reactivity in the reduction of benzylic alcohols to the corresponding benzyl radicals with terminal H-atom trapping to afford the deoxygenated product. Using the same method, we demonstrate access to synthetically versatile acyl radicals which enables the reduction of aromatic and aliphatic carboxylic acids to the corresponding aldehydes with exceptional chemoselectivity. This protocol also transforms carboxylic acids to heterocycles and cyclic ketones via intramolecular acyl radical cyclizations to forge new C–O, C–N and C–C bonds in a single step.

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