56698-00-1

Upstream product

• 98-89-5 Cyclohexanecarboxylic acid 
• 109-80-8 1.3-propanedithiol 
• 2043-61-0 cyclohexanecarbaldehyde 
• 108-94-1 cyclohexanone 
• 57529-04-1 2-chloro-1,3-dithiane 
• 931-50-0 cyclohexylmagnesium bromide 
• 18231-08-8 (dimethoxymethyl)cyclohexene 
• 7191-32-4 2,2-dibutyl-[1,3,2]dioxastanninane 
• 63830-87-5 2-trimethylsilyl-1-oxaspiro<2.5>octane 

Downstream Products

• 80402-90-0 2-cyclohexyl-2-trimethylsilylmethyl-1,3-dithiane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 329-29-3 cyclohexylmethylene difluoride 
• 37166-70-4 acetic acid 2-cyclohexyl-2-oxoethyl ester 
• 108-94-1 cyclohexanone 
• 1097189-56-4 2-(allyldimethylsilyl)-2-cyclohexyl-1,3-dithiane 

Relevant academic research and scientific papers

Novel method for incorporating the CHF2 group into organic molecules using BrF3

(Matrix presented) 2-Alkyl-1,3-dithiane derivatives, easily made from alkyl bromides and the parent 1,3-dithiane, were reacted with BrF3 to form the corresponding 1,1-difluoromethyl alkanes (RCHF2) in 60-75% yield. The reaction proceeds well with primary alkyl halides. The limiting step for secondary alkyl halides is the relatively low yield of the dithiane preparation. The two sulfur atoms of the dithiane are essential for the reaction.

Photocatalytic Reductive Radical-Polar Crossover for a Base-Free Corey–Seebach Reaction

A metal-free generation of carbanion nucleophiles is of prime importance in organic synthesis. Herein we report a photocatalytic approach to the Corey–Seebach reaction. The presented method operates under mild redox-neutral and base-free conditions giving the desired product with high functional group tolerance. The reaction is enabled by the combination of photo- and hydrogen atom transfer (HAT) catalysis. This catalytic merger allows a C?H to carbanion activation by the abstraction of a hydrogen atom followed by radical reduction. The generated nucleophilic intermediate is then capable of adding to carbonyl electrophiles. The obtained dithiane can be easily converted to the valuable α-hydroxy carbonyl in a subsequent step. The proposed reaction mechanism is supported by emission quenching, radical–radical homocoupling and deuterium labeling studies as well as by calculated redox-potentials and bond strengths.

Direct anodic (thio)acetalization of aldehydes with alcohols (thiols) under neutral conditions, and computational insight into the electrochemical formation of the acetals

A versatile protocol for the production of acetals/thioacetals by means of direct electrochemical oxidation is developed here under neutral conditions, providing (thio)acetals with good functional group tolerance and a wide scope for both aldehydes and (thio)alcohols. DFT calculations reveal that direct electron transfer from the anode plays a key role in carbonyl activation during this acid free acetalization process.

Visible-light promoted dithioacetalization of aldehydes with thiols under aerobic and photocatalyst-free conditions

A novel photocatalyst-free visible-light-mediated dithioacetalization of aldehydes and thiols has been developed. This protocol is operationally simple, mild and atom-economical, which provides an environmental benign access to dithioacetals at room temperature under aerobic conditions.

Graphene oxide (GO)-catalyzed chemoselective thioacetalization of aldehydes under solvent-free conditions

An efficient method for the synthesis of open chain, cyclic, and unsymmetrical dithioacetals from aryl/hetero-aryl/aliphatic aldehydes is described. The reaction is performed using graphene oxide (GO) as the catalyst under solvent-free and aerobic conditions. High chemoselectivity is observed in the reaction as aryl/alkyl ketones do not give thioketals under the condition.

Metal-free CH bond activation of branched aldehydes with a hypervalent iodine(III) catalyst under visible-light photolysis: Successful trapping with electron-deficient olefins

Direct acyl radical formation of linear aldehydes (RCH2-CHO) and subsequent hydroacylation with electron-deficient olefins can be effected with various types of metal and nonmetal catalysts/reagents. In marked contrast however no successful reports on the use of branched aldehydes have been made thus far because of their strong tendency of generating alkyl radicals through the facile decarbonylation of acyl radicals. Here use of a hypervalent iodine(III) catalyst under visible light photolysis allows a mild way of generating acyl radicals from various branched aldehydes thereby giving the corresponding hydroacylated products almost exclusively. Another characteristic feature of this approach is the catalytic use of hypervalent iodine(III) reagent which is a rare example on the generation of radicals in hypervalent iodine chemistry.

Facile deprotection of dithioacetals by using a novel 1,4-benzoquinone/cat. NaI system

The combination of 1,4-benzoquinone and a catalytic amount of NaI was found to be effective for the deprotection of dithioacetals. The reactions proceeded efficiently under mild, near-neutral reaction conditions, producing a wide range of aryl and alkyl aldehydes and ketones generally in high yields with good functional group compatibility. The method developed therefore represents a general, facile, and highly applicable approach for deprotecting dithioacetals.

Efficient and chemoselective acetalization and thioacetalization of carbonyls and subsequent deprotection using InF3 as a reusable catalyst

An efficient and chemoselective method for preparation of acetals and dithioacetals of aldehydes and their deprotection under catalysis of InF 3 is described.

Towards bis(acylsilanes) and cyclic unsaturated acylsilanes via metathesis: an exploratory study

New acyl(allyl)- and acyl(vinyl)silanes have been synthesized in order to explore cross metathesis or ring-closing metathesis as a new way towards bis(acyl)silanes or unsaturated cyclic acylsilanes, respectively. Metathesis from acylsilanes did not work b

New 6-oxa-2-silabicyclo[2.2.0]hexanes by photochemical conversion of acyl(allyl)(dimethyl)silanes

Under UV irradiation in acetonitrile, acyl(allyl)silanes undergo an intramolecular (2+2) cycloaddition (Paterno-Buechi type reaction) to give unprecedented 1-alkyl-6-oxa-2-silabicyclo[2.2.0] hexanes. The Royal Society of Chemistry.