1092506-86-9

Upstream product

• 15500-76-2 Dimethyl-dimedon-mono-(toluol-4-sulfonyl-hydrazon) 
• 13855-90-8 2,2,5,5-tetramethylcyclohex-3-en-1-one 
• 1083308-96-6 (1S)-2,2,5,5-tetramethylcyclohex-3-en-1-ol 

Downstream Products

• 1092506-85-8 (3R,4R)-3,4-dibromo-2,2,5,5-tetramethylcyclohexanone 
• 1092506-87-0 1(S)-acetoxy-(3R,4R)-dibromo-2,2,5,5-tetramethylcyclohexane 
• 53179-78-5 2,2-dimethyl-3R-(2',2'-dibromovinyl)-cyclopropane-1R-carboxylic acid 
• 26771-11-9 (1R)-cis-chrysanthemic acid 

Relevant academic research and scientific papers

Diastereoselective bromination of compounds bearing a cyclohex-3-enol moiety: Application to the enantioselective synthesis of (1R)-cis-deltamethrinic acid

(Chemical Equation Presented) (1R)-cis-Chrysanthemic acid has been prepared in a few steps with complete control of the relative and absolute stereochemistry. Some mechanistic aspect of the addition of bromine to the C,C double bond of 2,2,5,5-tetramethylcyclohex-3-enol is disclosed.

Syntheses of racemic and scalemic cis-chrysanthemic acid from β,γ-unsaturated cyclohexanol

2,2,5,5-Tetramethylcyclohexane-1,3-dione is a valuable starting-material precursor of cis-chrysanthemic acid. The (1S)-stereoisomer is a precursor of pyrethrin I, the most active natural insecticide from Chrysanthemum cinerariifolium, whereas the (1R)-stereoisomer is efficiently transformed to deltamethrin, the most active commercially available pyrethroid insecticide. Several intermediates have been identified and used with variable success for that purpose.