85611-92-3

Upstream product

• 109-99-9 tetrahydrofuran 
• 139-02-6 sodium phenoxide 
• 840-90-4 2-endo-norbornyl toluenesulfonate 
• 2534-77-2 exo-2-bromonorbornane 
• 498-66-8 norbornene 
• 108-95-2 phenol 
• 85564-63-2 ((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid (1S,2S,4R)-2-bicyclo[2.2.1]hept-2-yl-phenyl ester 
• 150-76-5 4-methoxy-phenol 
• 17152-43-1 o-Norborn-2-yl-phenol 
• 85564-64-3 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S,4R)-2-bicyclo[2.2.1]hept-2-yl-phenyl ester 

Downstream Products

• 85564-65-4 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2R,4S)-2-bicyclo[2.2.1]hept-2-yl-phenyl ester 
• 85564-64-3 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S,4R)-2-bicyclo[2.2.1]hept-2-yl-phenyl ester 
• 85564-73-4 2-((1R,2R,4S)-2-Bicyclo[2.2.1]hept-2-yl-phenoxymethyl)-oxirane 
• 85611-93-4 (R) 2-exo-bicyclo<2,2,1>hept-2-yl phenol 
• 85564-73-4 (S)-2-((1R,2R,4S)-2-Bicyclo[2.2.1]hept-2-yl-phenoxymethyl)-oxirane 
• 85564-73-4 (αR, 2R) (2-exo-bicyclo<2,2,1>hept-2-ylphenoxy) methyloxirane 
• 85564-73-4 (S)-2-((1S,2S,4R)-2-Bicyclo[2.2.1]hept-2-yl-phenoxymethyl)-oxirane 
• 85564-74-5 (αS, 2R) (2-exo-bicyclo<2,2,1>hept-2-ylphenoxy) methyloxirane 
• 85564-68-7 (αR, 2R) 3-<2-(2-exo-bicyclo<2,2,1>hept-2-yl)phenoxy>-1,2-propanediol 
• 85564-70-1 (αS, 2R) 3-<2-(2-exo-bicyclo<2,2,1>hept-2-yl)phenoxy>-1,2-propanediol 
• 85564-69-8 (S)-4-((1R,2R,4S)-2-Bicyclo[2.2.1]hept-2-yl-phenoxymethyl)-2,2-dimethyl-[1,3]dioxolane 
• 85564-77-8 (S)-4-((1S,2S,4R)-2-Bicyclo[2.2.1]hept-2-yl-phenoxymethyl)-2,2-dimethyl-[1,3]dioxolane 
• 85564-76-7 (αS, 2R) 1-(2-exo-bicyclo<2,2,1>hept-2-ylphenoxy)-3-<(1-methylethyl)amino>-2-propanol 
• 85564-66-5 (αS, 2S) 1-(2-exo-bicyclo<2,2,1>hept-2-ylphenoxy)-3-<(1-methylethyl)amino>-2-propanol 

Relevant academic research and scientific papers

Iodoarene-Catalyzed Stereospecific Intramolecular sp3 C-H Amination: Reaction Development and Mechanistic Insights

A new strategy is reported for intramolecular sp3 C-H amination under mild reaction conditions using iodoarene as catalyst and m-CPBA as oxidant. This C-H functionalization involving iodine(III) reagents generated in situ occurs readily at sterically hindered tertiary C-H bonds. DFT (M06-2X) calculations show that the preferred pathway involves an iodonium cation intermediate and proceeds via an energetically concerted transition state, through hydride transfer followed by the spontaneous C-N bond formation. This leads to the experimentally observed amination at a chiral center without loss of stereochemical information.

Acid-Catalyzed Hydrolysis of Bridged Bi- and Tricyclic Compounds. XXVII. An Application of the Excess Acidity Method to the Norbornyl Cation Problem

Hydrolysis rates and products of exo- and endo-2-phenoxynorbornanes have been studied in concentrated aqueous perchloric acid solutions.The activation parameters, solvent deuterium isotope effects, dependences of the reation rates on acid concentration, products of hydrolysis and the high exo/endo rate ratio (2570) are all in agreement with the A-1 mechanism, in which the norbornyl cation is formed in the rate-limiting stage.The excess acidity method was used to determine first the pKa value (-5.56) and the slope parameter (m* = 1.01) for the oxygen protonation of the endo epimer, and then the slope parameters for the rate-limiting stages of the exo and endo hydrolyses (m* = 1.37 and 1.55, respectively).The slope parameters are somewhat exceptional, and may hint at a more delocalized charge in the transition state of the exo hydrolysis.

REACTION OF exo-2-NORBORNYL AND 1-ADAMANTYL p-TOLUENESULFONATES WITH SODIUM PHENOXIDE IN TETRAHYDROFORAN. IONIZATION OF THE SUBSTRATES UNDER "APPARENTLY-SN2" CONDITIONS

exo-2-Norbornyl and 1-adamantyl tosylates react with sodium phenoxide in tetrahydrofuran via ionization, most probably through a cyclic transition state.The results call for attention in interpreting substitution reactions under "apperently-SN2" conditions.