63142-57-4

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 55667-43-1 1,1-dichloro-4-methyl-penta-1,3-diene 
• 75-62-7 Bromotrichloromethane 
• 66692-75-9 ethyl 3-formyl-2,2-dimethylcyclopropanecarboxylate 
• 65771-92-8 3-methyl-3-chloro-2-(2',2'-dichlorovinyl)-butanecarboxylic acid ethyl ester 
• 64788-83-6 ethyl trans-3-(1-hydroxy-2,2,2-trichloroethyl)-2,2-dimethylcyclopropanecarboxylate 
• 118171-47-4 ethyl trans-3-(1-acetoxy-2,2,2-trichloroethyl)-2,2-dimethylcyclopropanecarboxylate 
• 59897-92-6 ethyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoate 
• 60066-53-7 ethyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate 
• 60066-54-8 ethyl 4-bromo-6,6,6-trichloro-3,3-dimethylhexanoate 
• 7796-72-7 ethyl 3,3-dimethylpent-4-enoate 
• 63142-59-6 4-(2,2-dichloroethenyl)dihydro-5,5-dimethyl-2(3H)-furanone 
• 38692-37-4 ethyl (±)-(1R,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylate 
• 63435-29-0 ethyl 6,6,6-trichloro-3,3-dimethyl-4-hexenoate 

Downstream Products

• 63406-19-9 ethyl cis-2-(2-chlorethynyl)-3,3-dimethylcyclopropanecarboxylate 
• 133575-08-3 ethyl trans-3-<(Z)-2-chloro-2-phenylethenyl>-2,2-dimethylcyclopropanecarboxylate 
• 133472-20-5 ethyl trans-3-<2,2-di(1-hexynyl)ethenyl>-2,2-dimethylcyclopropanecarboxylate 
• 133472-19-2 ethyl trans-3-<(Z)-3-chloro-2-(3-chlorophenyl)ethenyl>-2,2-dimethylcyclopropanecarboxylate 
• 78479-01-3 ethyl trans-3-<(Z)-2-chloro-2-(4-chlorophenyl)ethenyl>-2,2-dimethylcyclopropanecarboxylate 

Relevant academic research and scientific papers

Reductive Addition of Polyhalomethanes and Their Related Compounds to Aldehydes and 1,2-Elimination of the Coupling Products in a Pb/Al Bimetal Redox System

A Pb/Al bimetal system was used to carry out reductive addition of tetrachloromethane, tetrabromomethane, bromotrichloromethane, trichloroacetamide, and trichloroacetonitrile to aldehydes.Subsequent 1,2-elimination of the halogen atom and hydroxyl group from the coupling products was also performed with the Pb/Al bimetal system.The technology was successfully applied to stereocontrolled syntheses of ethyl trans- and cis-3-(2,2-dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates.

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.

TRANSITION-METAL-CATALYSED REACTIONS OF DIAZOESTERS : SYNTHESIS OF CHRYSANTHEMIC AND PERMETHRIC ACID ESTERS BY CYCLOPROPANATION OF CONJUGATED DIENES

Pyrethroid precursors (permethric and chrysanthemic acid esters) are efficiently synthesized by rhodium(II)-catalysed cyclopropanation of the properly substituted conjugated diene.Reaction selectivities depend on both the catalyst counter-ion and the diazoester alkoxy-group (carbene precursor) and are attributed to non-bonded interactions.