20351-71-7

Upstream product

• 100-61-8 N-methylaniline 
• 1005-56-7 phenylcarbonochloridothioate 
• 463-71-8 thiophosgene 
• 108-95-2 phenol 
• 121-69-7 N,N-dimethyl-aniline 

Downstream Products

• 1934-92-5 N-methyl-N-phenyl-benzamide 

Relevant academic research and scientific papers

First-class amine thioformate derivative and synthesis method thereof

The invention discloses a first-class amine thioformate derivative and a synthesis method thereof. The derivative has a structure shown as a formula (I). According to the synthesis method, amine thionyl fluoride is used as raw materials; copper salt is us

Kinetic Control over CdS Nanocrystal Nucleation Using a Library of Thiocarbonates, Thiocarbamates, and Thioureas

We report a family of substituted thiocarbonates, thiocarbamates, and thioureas and their reaction with cadmium oleate at 180-240 °C to form zincblende CdS nanocrystals (d = 2.2-5.9 nm). To monitor the kinetics of CdS formation with UV-vis spectroscopy, t

Lewis base catalysis by thiourea: N -bromosuccinimide-mediated oxidation of alcohols

In recent times, (thio)urea derivatives have become synonymous with hydrogen bonding owing to their extensive applicability as small molecule organocatalysts. In this paper, another activation mode by thiourea derivatives, namely via Lewis base catalysis, is disclosed for the NBS-mediated oxidation of alcohols. The mild reaction conditions employed here is suitable for chemoselective oxidation of secondary alcohol in the presence of primary alcohol.

Radical OfC transposition: A metal-free process for conversion of phenols into benzoates and benzamides

We report a metal-free procedure for transformation of phenols into esters and amides of benzoic acids via a new radical cascade. Diaryl thiocarbonates and thiocarbamates, available in a single high-yielding step from phenols, selectively add silyl radicals at the sulfur atom of the CdS moiety. This addition step, analogous to the first step of the Barton-McCombie reaction, produces a carbon radical which undergoes 1,2 OfC transposition through an O-neophyl rearrangement. The usually unfavorable equilibrium in the reversible rearrangement step is shifted forward via a highly exothermic C-S bond scission in the O-centered radical, which furnishes the final benzoic ester or benzamide product. The metal-free preparation of benzoic acid derivatives from phenols provides a potentially useful alternative to metal-catalyzed carbonylation of aryl triflates.

DIRECT CONVERSION OF PHENOLS INTO AMIDES AND ESTERS OF BENZOIC ACID

A method is provided for the preparation of an aromatic carboxylic acid aryl ester or an N-aryl aromatic carboxamide. The method comprises contacting an O,O-diaryl thiocarbonate or an O-aryl-N-aryl thiocarbamate with a reactant that regioselectively reacts with sulfur, which contact causes an O-neophyl rearrangement, thereby forming either the aromatic carboxylic acid aryl ester or the N-aryl aromatic carboxamide, respectively.

Metal-free transformation of phenols into substituted benzamides: A highly selective radical 1,2-O→C transposition in O-aryl-N-phenylthiocarbamates

Radical merry-go-round: A highly efficient metal-free transformation of phenols into benzamides is designed through one-step conversion of phenols to aryl thiocarbamates and a subsequent radical addition/rearrangement/ fragmentation cascade. Computational analysis fully rationalizes the experimentally observed selectivity. Despite the possible competition from N-C fragmentation and N-neophyl rearrangement, the transformation exclusively follows the most kinetically and thermodynamically favored O-neophyl rearrangement path.

Phenyl chloro(thionoformate): A new dealkylating agent of tertiary amines

Phenyl chloro(thionoformate) reacts rapidly with unhindered tertiary aliphatic amines at 20° to give a thiocarbamate and an alkyl chloride. Dialkylcyclohexylamines react surprisingly rapidly to form predominantly cyclohexene. The thiocarbamates are converted into the secondary amine salt by treatment with dimethyl sulfate, followed by hydrolysis with water. Rates of reaction and alkyl group cleavage selectivity in amines were found to be superior or comparable to those previously reported with chloroformates.

The dealkylation of tertiary aliphatic amines with phenyl chlorothionoformate

Phenyl chlorothionoformate reacts reacts rapidly with aliphatic amines at 20°C to give a thiourethane and an alkyl chloride. The urethanes are readily converted to the secondary amine salt by reaction with dimethyl sulfate, followed by hydrolysis with wat