87923-86-2

Upstream product

• 73462-83-6 (-)-endo-bornyl-1,2,4-triazoline-3,5-dione 
• 87923-82-8 cis-1-phenyl-8-thiabicyclo<4.3.0>non-3-ene 8,8-dioxide 
• 87923-83-9 cis-1-phenyl-7,8-dimethylbicyclo<4.2.0>octa-3,7-diene 
• 588-59-0 stilbene 

Downstream Products

• 344931-19-7 1,8-dimethyl-2-phenylcyclooctatetraene 
• 87923-78-2 (-)-1,2-dimethyl-3-phenylcyclooctatetraene 

Relevant academic research and scientific papers

Bond Fixation in Annulenes. 16. Synthesis of the 1,2-Dimethyl-3-phenylcyclooctatetraene ->/<- 1,8-Dimethyl-2-phenylcyclooctatetraene Bond Shift Isomer Pair. Probe of the Relative Size of a Flanking Phenyl Substituent by means of Racemization Kinetics

Two synthetic approaches to the cyclooctatetrene bond shift isomers 3 ->/octadiene to generate the cyclooctatetraene nucleus.Although 3 dominates over 4 in the equilibrium, it is possible to separate these bond shift isomers by cycloaddition with a triazolinedione.When recourse was made to the endo-bornyl-substituted dienophile, it was ultimately possible to obtain (-)-3 and to determine its rate of racemization.The data indicate that the flanking phenyl group in 3 causes significant rate retardation relative to the trimethyl derivative.This finding contrasts with the behavior of 2 which racemizes more rapidly despite an interstitial phenyl substituent.The source of these dissimilar effects has been clarified by MM2 calculations, the details of which are presented.