371-90-4

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 84, p. 4275, 1962 DOI: 10.1021/ja00881a017Tetrahedron, 27, p. 3965, 1971

InChI:InChI=1/C6H10F2/c7-6(8)4-2-1-3-5-6/h1-5H2

Upstream product

• 108-94-1 cyclohexanone 
• 699-64-9 <1-Fluorcyclohexyl>-fluorformiat 
• 2108-92-1 1,1-dichlrocyclohexane 
• 29443-47-8 1,1-diiodocyclohexane 
• 100-64-1 cyclohexanone-oxime 
• 695-64-7 1-chloro-1-nitrosocyclohexane 
• 1528-30-9 methylenecyclopentane 
• 115869-06-2 1,1-bis(trifluoroacetoxy)cyclohexane 
• 694-51-9 1-fluorocyclohexene 
• 22780-08-1 1,1-bis(trichloroacetoxy)cyclohexane 
• 95652-97-4 1,1-diacetoxycyclohexane 
• 407-25-0 trifluoroacetic anhydride 
• 930-66-5 1-chlorocyclohexene 

Downstream Products

• 2108-92-1 1,1-dichlrocyclohexane 
• 694-51-9 1-fluorocyclohexene 
• 462-06-6 fluorobenzene 
• 71-43-2 benzene 
• 110-83-8 cyclohexene 
• 110-82-7 cyclohexane 

Relevant academic research and scientific papers

METHOD FOR MANUFACTURING DIFLUOROMETHYLENE COMPOUND

The problem to be solved by the present invention is to provide a novel method for producing a difluoromethylene compound. This problem is solved by a method for producing a difluoromethylene compound containing a —CF2— moiety, the method comprising step A of mixing: a) a carbonyl compound containing a —C(O)— moiety;b) optionally an amine;c) a fluoride represented by the formula: MF, wherein M represents a Group 1 element of the periodic table;d) a halogenated fluorine compound represented by the formula: XFn, wherein X represents chlorine, bromine, or iodine, and n is a natural number of 1 to 5; ande) sulfur chloride.

Arylsulfur chlorotetrafluorides as useful fluorinating agents: Deoxo- and dethioxo-fluorinations

Usage of arylsulfur chlorotetrafluorides 1 as versatile deoxo- and dethioxo-fluorinating agents is described. There have been developed two convenient methods for the in situ preparation of reactive arylsulfur trifluorides 2 from 1. The one is reduction of 1 with a reducer such as pyridine to 2, and the other is disproportionation of 1 with a diaryl disulfide to 2 with evolution of chlorine gas. The latter method is a convenient way to get neat 2 from 1. The in situ prepared 2 fluorinates many kinds of substrates such as alcohols, aldehydes, ketones, diketones, and carboxylic acids to give the corresponding CF, CF2, CF2CF2, and CF 3 compounds in high yields. 2 also fluorinates various sulfur compounds including CS groups to give CF2, OCF2, CF 3, and OCF3 compounds in high yields. Reactions of 2 with diols or bis(trimethylsilyl) derivatives of diols or amino alcohols provided the corresponding deoxofluoro-arylsulfinylation products in high yields. In addition, it has been found that chlorotetrafluorides 1 directly and effectively react with the sulfur compounds to give the corresponding fluoro compounds in high yields. Since they are the intermediates for the production of industrially useful arylsulfur pentafluorides, arylsulfur chlorotetrafluorides 1, in particular, phenylsulfur chlorotetrafluoride (1a) are expected to find use as inexpensive and versatile deoxo- and dethioxo-fluorinating agents for the preparation of many organofluoro compounds.

Practical synthesis of gem-difluorides from cyclohexanone: Synthesis of gem-bistrifluoroacetates and their reactions with fluoride nucleophiles

Formation of ketone acylals bearing trihaloacetoxy groups and their nucleophilic geminal disubstitution by fluoride ions were investigated. Cyclohexanone reacted with trifluoroacetic anhydride without catalyst to give gem-bistrifluoroacetates via a concerted bimolecular reaction. Treatment with hydrogen fluoride under mild conditions efficiently yielded the corresponding gem-difluorides. In this reaction process, trifluoroacetic acid was recovered and converted to trifluoroacetic anhydride using P2O5. Since gem-difluorides were derived from ketones, HF and P2O5, this constitutes a practical synthesis of gem-difluorides.

Reaction of chlorosulfonyl isocyanate with fluorosubstituted alkenes: Evidence of a concerted pathway

Concerted reactions are indicated for the electrophilic addition of chlorosulfonyl isocyanate with monofluoroalkenes. A vinyl fluorine atom on an alkene raises the energy of a stepwise transition state more than the energy of the competing concerted pathw

FLUORINATION PROCESSES WITH ARYLSULFUR HALOTETRAFLUORIDES

New fluorination processes for introducing one or more fluorine atoms into target substrate compounds with arylsulfur halotetrafluorides are disclosed. Also disclosed are methods for preparation of arylsulfur trifluorides.

SUBSTITUTED PHENYLSULFUR TRIFLUORIDE AND OTHER LIKE FLUORINATING AGENTS

Novel substituted phenylsulfur trifluorides that act as fluorinating agents are disclosed. Also disclosed are methods for their preparation and methods for their use in introducing one or more fluorine atoms into target substrate compounds.

Substituted phenylsulfur trifluoride and other like fluorinating agents

Novel substituted phenylsulfur trifluorides that act as fluorinating agents are disclosed. Also disclosed are methods for their preparation and methods for their use in introducing one or more fluorine atoms into target substrate compounds.

METHOD OF FLUORINATION

A method of fluorination comprising reacting monosaccharides, oligosaccharides, polysaccharides, composite saccharides formed by bonding of these saccharides with proteins and lipids and saccharides having polyalcohols, aldehydes, ketones and acids of the polyalcohols, and derivatives and condensates of these compounds with a fluorinating agent represented by general formula (I) thermally or under irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region. In accordance with the method, the fluorination at a selected position can be conducted safely at a temperature in the range of 150 to 200°C where the reaction is difficult in accordance with conventional methods. The above method comprising the irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region can be applied to substrates other than saccharides. When a complex compound comprising HF and a base is reacted under irradiation with microwave, fluorination at a specific position which is difficult in accordance with conventional methods proceeds highly selectively, efficiently in a short time and safely.

Process for producing alpha, alpha-difluorocycloalkane compound

A method for producing an α,α-difluorocycloalkane at high purity with good efficiency, which comprises a step of treating a fluorocycloalkene with hydrogen fluoride wherein the fluorocycloalkene has one fluorine atom directly bonded to a carbon atom of carbon-carbon unsaturated double bond, more preferably, a step of directly adding the hydrogen fluoride to a reaction mixture obtained by treating the cycloalkanone with the de-oxygen fluorinating agent.

2,2-Difluoro-1,3-dimethylimidazolidine (DFI). A new fluorinating agent

2,2-Difluoro-1,3-dimethylimidazolidine (DFI) is a new deoxo-fluorinating agent that is useful for the conversion of alcohols to monofluorides, and aldehydes/ketones to gem-difluorides under mild conditions.