17336-81-1

Upstream product

• 822-87-7 2-Chlorocyclohexanone 
• 18709-01-8 cyclohexanone-2-carboxylic acid 
• 55949-64-9 1,6-Dichlor-7-oxabicyclo<4.1.0>heptan 
• 108-94-1 cyclohexanone 

Downstream Products

• 6498-39-1 2-chlorocyclohex-2-en-1-ol 
• 3400-88-2 2-chlorocyclohex-2-en-1-one 
• 91446-60-5 2-chloro-cyclohex-2-enone-(2,4-dinitro-phenylhydrazone) 
• 10557-33-2 cis-2,6-dichlorocyclohexanone 

Relevant academic research and scientific papers

4+3 Cycloaddition reactions of halogen-substituted cyclohexenyl oxyallylic cations

2,6-Dibromo- and 2,2-dichlorocyclohexanone react with base in the presence of various dienes to give 4+3 cycloadducts in fair to good yields. Preliminary studies of the cycloadducts suggest that they are unstable and are recalcitrant to nucleophilic addit

Extending the haloform reaction to non-methyl ketones: Oxidative cleavage of cycloalkanones to dicarboxylic acids using sodium hypochlorite under phase transfer catalysis conditions

Cyclohexanone is readily oxidized to adipic, α,α-dichloroadipic, glutaric and succinic acids by sodium hypochlorite under phase transfer conditions. The selectivity is highly dependent on the pH of the reacting system. A consecutive chlorination-hydrolysis mechanism is proposed in which only cyclohexanone is a reactive substrate leading in parallel to the melange of oxidized products. Cyclooctanone and cyclopentanone are similarly oxidized.

Preparation of chiral allylic alcohols using Rhizopus nigricans. Use of the Harada-Nakanishi exciton chirality method for verifying configurational assignments of allylic alcohols

A series of (R) acyclic and cyclic allylic alcohols was prepared by enantioselective hydrolysis of acetates using Rhizopus nigricans.The configurations of the alcohols formed were established by chemical methods and, in the case of 1,2-benzocyclohepta-1,3

Reactions of alicyclic ketones in carbon tetrachloride. II. Kinetics of the chlorination of 2-chlorocyclopentanone and 2-chlorocyclohexanone, catalyzed by hydrogen chloride

The kinetics of the direct chlorination of 2-chlorocyclopentanone (2-mccp) and 2-chlorocyclohexanone (2-mcch) in carbon tetrachloride, catalyzed by hydrogen chloride, were studied.Reaction products are all the possible 2,2-, 2,5-, and 2,6-dichloro compounds.The ratios depend on the concentrations of the monochloro compound and hydrogen chloride.Surprisingly, even at conversions of the monochloro compound as low as 2percent, 2,2,5-trichlorocyclopentanone and 2,2,6-trichlorocyclohexanone, respectively, are also formed.The chlorination of both monochloro ketones shows zero order in chlorine.The order in hydrogen chloride is 1.3.The order in 2-mccp and 2-mcch varies somewhat with the concentration of the ketone and was found to be roughly 1.7.The variation in reaction order is explained by a partial self-association of the ketones.The ketones act as substrates as well as basic catalysts in the rate-determining α- or α'-carbon deprotonation.General base catalysis is clearly demonstrated by a strong increase in the rate of chlorination of 2-mccp upon addition of cyclopentanone (cp) to the reaction mixture, which agrees with the mechanism as presented in a previous paper.Kinetic equations derived from the reaction models for the "separate" and "mixed" ketone chlorinations accurately describe the observed rates of the chlorination of 2-mccp and 2-mcch in the concentration range of 0.04 - 1.0 M.

PRACTICAL SYNTHESIS OF 2,2,5,5-TETRACHLORO-1,6-HEXANEDIOIC ACID, FROM TRANS-1,2-CYCLOHEXANEDIOL OR CYCLOHEXANONE, INVOLVING OXIDATION OF 3,3,6,6-TETRACHLORO-1,2-CYCLOHEXANEDIONE

Trans-1,2-cyclohexanediol was quantitatively converted into 3,3,6,6-tetrachloro-1,2-cyclohexanedione (2) by treatment with chlorine in dimethylformamide.The hydrate of the dione was oxidized by aqueous potassium permanganate to afford the title acid 1 in 91percent overall yield.An alternative low cost preparation was elaborated, providing 2 in 61-74percent yield starting from cyclohexanone in a three step procedure without isolation of intermediates.The reaction seqence involves substitution of α-dichloro- and trichlorocyclohexanones by sodium acetate in acetic acid and chlorination of the resulting 2-hydroxy- and 2-acetoxy-2-cyclohexenones in dimethylformamide.

Halogen Epoxides, 3. Reactions of 2-Chloro- and 2,3-Dichlorooxiranes with Silver Tetrafluoroborate: Synthesis of α-Fluorinated Carbonyl Compounds

Reactions of chlorinated oxiranes with silver tetrafluoroborate in ether have been investigated.Substituted-2-chlorooxiranes (4a - e) afforded the corresponding α-fluorocarbonyl compounds (7a - e) as major products and the isomeric α-chlorocarbonyl compounds (8a - e) as minor products.Substituted 2,3-dichlorooxiranes (10, 14, 20, 24) yielded the isomeric α,α-dichloroketones (13, 19, 22, 26b, 29b) as well as the corresponding α-chloro-α-fluoroketones (12, 17, 21, 26a, 29a) and α,β-unsaturated α-chloroketones (18, 23, 27, 30).The course of the reaction was rationalized.Similar reaction with α-chloroketones and with α,α-dichloroketones succeeded only at substrates (8b, 35) in which the chlorine substituents were in benzylic positions.