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• 13712-75-9 3-methyl-2,4-diphenyloxazolium-5-olate 
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• 21737-87-1 N-methyl benzimidoyl chloride 
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• 5310-14-5 N-methylthiobenzamide 
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• 3376-23-6 N-methyl-α-phenylnitrone 

Relevant academic research and scientific papers

The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide

In order to understand the antiaromaticity of maleimides, the enthalpies of formation and sublimation of N-methylmaleimide, N-methylsuccinimide, N-methylphthalimide, and N-benzoyl-N-methylbenzamide were measured. The numerical values of enthalpies of formation for these compounds in the solid state are -329,3 ± 1.4, -469.8 ± 1.6, -325.0 ± 2.1, and -239.6 ± 3.8 kJ mol-1, respectively, while the corresponding values in the gaseous state are -256.0 ± 1.5, -389.7 ± 1.6, -233.9 ± 2.2, and -119.5 ± 3.8 kJ mol-1, respectively. The values of enthalpies of sublimation for the same compounds are 73.3 ± 0.5, 80.1 ± 0.3, 91.1 ± 0.5, and 120.1 ± 0.4 kJ mol-1, respectively. We find that the antiaromaticity of maleimides is only modest.

Synthesis of N-Acyl Sulfamates from Fluorosulfates and Amides

A novel synthetic strategy toward N-acyl sulfamates was developed. Interestingly, fluorosulfates, a new emerging class of electrophiles, were used to construct the sulfamate core. This precludes handling of chlorosulfonyl isocyanate and sulfamoyl chloride

I2/Aqueous TBHP-Catalyzed Coupling of Amides with Methylarenes/Aldehydes/Alcohols: Metal-Free Synthesis of Imides

We present a metal-free method for the synthesis of imides by the direct coupling of NH-amides with methylarenes under iodine/aqueous TBHP conditions. The optimized conditions worked very well with benzaldehydes and benzyl alcohol and furnished the corresponding imides in good to excellent yields. A series of control and radical scavenger experiments were also performed, which suggested the involvement of radical pathways. The labeling experiment in the presence of 18O-labeled H2O suggested water as a source of oxygen in the imides.

TBHP/TEMPO-mediated oxidative synthesis of imides from amides

A new protocol for the synthesis of imides has been developed. In the presence of copper catalyst, N-benzylamides were oxidized to the corresponding imides by TBHP/TEMPO system in moderate to good yields. Imides were synthesized through the oxidation of N-benzylamides by TBHP/TEMPO system in moderate to good yields.

Copper-catalyzed synthesis of imides from aldehydes or alcohols and amine hydrochloride salts

An efficient approach to imides has been developed. With tert-butyl hydroperoxide (TBHP) as the oxidant, CuBr (20 mol-%) as the catalyst, and PhI(OAc)2 (50 mol-%) as the additive, aldehydes or alcohols reacted with amine hydrochloride salts to provide imides in moderate to good yields. A possible reaction pathway for the formation of the products is also discussed in this paper.

Peroxidation of C-H bonds adjacent to an amide nitrogen atom under mild conditions

Under mild conditions, the oxidative functionalization of C-H bonds adjacent to an amide nitrogen atom was achieved. tert-Butylperoxyamido acetal was obtained in high yields and could be further converted into α-substituted amides by treatment with Grigna

Oxidation of benzylamines to amides

A convenient method for the conversion of tertiary benzylamines to benzamides by phase transfer oxidation is described. Yields are good. Regioselectivities are reported.

Preparation of imides

Cyclic imides are prepared by reacting carbon monoxide with an ortho dihalide aromatic compound or a cis-1,2-vinyl dihalide and an amine in the presence of palladium catalyst and a base. The process is preferably conducted in the presence of a dipolar aprotic solvent as a liquid reaction medium. Acyclic imides are prepared by reacting CO with an activated halide and an amide (primary or secondary) in the presence of a Pd catalyst and a base.

PHOTOCHEMICAL AND THERMAL REACTIONS OF HETEROCYCLES. IV. PHOTO-OXIDATION REACTIONS OF MESOIONIC DITHIOLIUMOLATE, THIAZOLIUMOLATE, AND RELATED HETEROCYCLES. SOLVENT EFFECTS ON THE COURSE OF THE PHOTO-OXIDATION

Photo-oxidation of mesoionic 1,3-dithiolium-4-olates (1) gave diacyl disulfide (2), and that of a mesoionic thiazolium-4-olate (6) and oxazolium-5-olate (9) gave diacylamides as the main products.The formation of these products was rationalized by a route involving fragmentation of the corresponding endoperoxides, which are formed by cycloaddition of singlet oxygen on the mesoionic rings.Photo-oxidation of 5(4H)-oxazolones (12) and a 5(4H)-thiazolone (17) in dichloromethane gave the corresponding dehydro-dimers, while that of the former in dimethylformamide gave mainly diacylamides.The acylamides were considered to arise via the endoperoxides of the mesoionic tautomers.

PHOSPHORIC-CARBOXYLIC IMIDES. III. THE BENZOYLATION OF N-METHYLDIETHYLPHOSPHORAMIDATE AND RELATED ANIONS

The synthetic route to mixed phosphoric-carboxylic imides (1) via the N-acylation of phosphoramidates was investigated.The reaction of PhC(O)X(X = Br, Cl, F) with conjugate base of (EtO)2P(O)NHMe (2) yields three products: PhCO2Et (3), PhC(O)NHMe (4) and (PHCO)2NMe (5). (4) and (5) are formed via the initial rapid formation of (1), while (3) results from the ElcB raction of (2).The attack of various nucleophilic species at mixed imide (1) was studied, and the possible mechanisms of the P-N bond cleavage, followed by the transfer of nitrogen from phosphoryl to the carbonyl centre, are discussed.