60066-53-7

Usage

InChI:InChI=1/C10H16Cl4O2/c1-4-16-8(15)6-9(2,3)7(11)5-10(12,13)14/h7H,4-6H2,1-3H3

Upstream product

• 56-23-5 tetrachloromethane 
• 7796-72-7 ethyl 3,3-dimethylpent-4-enoate 
• 109-73-9 N-butylamine 

Downstream Products

• 60066-84-4 ethyl 2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate 
• 63142-57-4 ethyl (+/-)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 63142-56-3 ethyl (+/-)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 59609-49-3 ethyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 60066-84-4 ethyl 2,2-dimethyl-3-(2,2,2-trichloroethyl)-cyclopropanecarboxylate 

Relevant academic research and scientific papers

Studies on sulfinatodehalogenation: The addition reaction of halocarbons with olefins initiated by sodium dithionite

Halocarbons such as carbon tetrachloride, CCl3Br, CF3CCl3, BrCF2CF2Br, BrCF2CFClBr and CF2Br2, reacted with olefins in the presence of the sulfinatodehalogenation reagent sodium dithionite under mild conditions to give the corresponding adducts. In the case of F113, CFCl2CF2CFCl2 and CF3Cl3, the polyfluoroalkylation product resulted.

Process for preparing halogenated compounds

A process for preparing halogenated compounds of formula RCY(Z)CH2 CH(X)C(CH3)CH2 COR1 where X, Y and Z are halo, R is alkyl, halo, haloalkyl or aryl, and R1 is hydroxy, halo, alkoxy, alkyl or haloalkyl, or the residue of a pyrethroidal alcohol, in which a compound of formula CH2 =CHC(CH3)2 COR1 is reacted with a sulphonyl halide of formula RCY(Z)SO2 X. The process avoids the use of volatile halocarbons in the production of valuable intermediates for insecticides.

A Convenient Synthesis of Ethyl 3-(2,2-Dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates and Its Modifications for cis-Isomer Enrichment

A synthesis of the title compounds 5 involves the reaction between 3-methyl-2-buten-1-ol and triethyl orthoacetate to produce ethyl 3,3-dimethyl-4-pentenoate, which is followed by the addition of various carbon tetrahalides to the double bond.The reaction of resulting adducts with a base affords 5 in high yields.Stereoselective preparation of the cis-isomer was achieved by the following two methods: First one involves selective transformation of ethyl 4-bromo-6,6,6-trichloro-3,3-dimethylhexanoate to ethyl 6,6,6-trichloro-2,3-dimethyl-4-hexanoate (8a) with piperidine followed by the selective conversion of 8a to cis-2,2-dichloroethenyl compound (cis-5a).Second one is based on the stereoselective cyclization of ethyl 4,6,6,6-tetrachloro-3,3-dimethyl-hexanoate (t-BuONa/solvent/HMPA) to ethyl cis-2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate which is transformed into cis-5a without cis-trans isomerisation.

Method of producing cyclopropanecarboxylic acids and esters

Novel γ-lactone derivatives are provided. These lactone derivatives, when reacted with hydrogen halide in alcohol, yield γ-halogeno-δ-unsaturated carboxylic acid esters. This ring-opening process is useful for the purpose of increasing the yield of pyrethrin analogs which are of value as insecticides and agricultural chemicals. Thus, the γ-lactone derivatives by-produced in the production process for dihalogenovinyl chrysanthemumates are caused to undergo ring-opening reaction to yield the corresponding γ-halogeno-δ-unsaturated carboxylic acid esters which are important intermediates for said pyrethrin analogs.

Process for preparing dihalovinylcyclopropanecarboxylates

Novel syntheses of dihalovinylcyclopropanecarboxylates, including potent insecticides, are described. The processes begin with the reaction between an alkenol and an orthoester to produce a γ-unsaturated carboxylate, followed by the catalyzed addition of a carbon tetrahalide to the double bond and dehydrohalogenation to produce a cyclopropane derivative.