143192-93-2

Upstream product

• 5164-64-7 bicyclo[2.1.1]hexan-2-one 
• 143192-91-0 2-Pentafluorethylbicyclo<2.1.1>hex-2-yl-trifluormethansulfonat 
• 143192-94-3 1-Pentafluorethylbicyclo<2.1.1>hex-2-yl-trifluormethansulfonat 
• 143192-99-8 2-Azido-1-pentafluoroethyl-bicyclo[2.1.1]hexane 
• 143193-00-4 1-Pentafluoroethyl-bicyclo[2.1.1]hex-2-ylamine 
• 143192-89-6 2-(Pentafluoroethyl)bicyclo<2.1.1>hexan-2-ol 
• 143192-96-5 1-Pentafluorethylbicyclo<2.1.1>hexan-2-ol 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 143192-90-9 2-Pentafluorethylbicyclo<2.1.1>hex-2-yl-4-brombenzolsulfonat 

Relevant academic research and scientific papers

Reactions of Pentafluoroethyl-Substituted Bicyclohexane Derivatives

The effect of inductively electron-withdrawing substituents on the generation of 2-bicyclohexyl cations was probed by means of pentafluoroethyl groups. 2-Pentafluoroethyl-2-bicyclohexyl brosylate (4a) and triflate (4b) were found to rearrange with formation of the analogous 1-pentafluoroethyl-2-bicyclohexyl sulfonates 5a, b.Solvolytic displacement did not compete with the rearrangement but occurred on 5b at elevated temperatures.Deuterium labels revealed that the rearrangement proceeded stereospecifically, with the sulfonate departing and rebonding on the same side of the molecular plane.Complete inversion was obser ved during solvolysis of 5b in aqueous dioxane while some retention (16percent) occurred in trifluoroacetic acid.Predominant inversion even with the analogous diazonium ion in water attests to the reluctant formation of 1-pentafluoroethyl-2-bicyclohexyl cations.Solvolysis rates of 4a, b and 5b were in close agreement with those of the analogous cyano derivatives, thus confirming that the resonance interaction of α-cyano groups with carbocations is small. Key Words: Carbocations, destabilized / Solvolysis rates / Wagner-Meerwein rearrangement / Substitution, nucleophilic