75211-13-1

Basic information

• Product Name: Bicyclo[2.2.1]heptane, 2-phenoxy-
• CAS NO: 75211-13-1
• Molecular Formula: C13H16O
• Molecular Weight: 188.269
• Mol File: 75211-13-1.mol

Chemical Properties

• CAS DataBase Reference: Bicyclo[2.2.1]heptane, 2-phenoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.1]heptane, 2-phenoxy-(75211-13-1)
• EPA Substance Registry System: Bicyclo[2.2.1]heptane, 2-phenoxy-(75211-13-1)

Safety Data

• Hazardous Substances Data: 75211-13-1(Hazardous Substances Data)

Upstream product

• 109-99-9 tetrahydrofuran 
• 139-02-6 sodium phenoxide 
• 840-90-4 2-endo-norbornyl toluenesulfonate 
• 498-66-8 norborn-2-ene 
• 108-95-2 phenol 
• 498-66-8 norbornene 
• 2534-77-2 exo-2-bromonorbornane 
• 108-86-1 bromobenzene 

Downstream Products

• 497-36-9 Norborneol 
• 108-95-2 phenol 
• 497-37-0 exo-2-norbornanol 

Relevant articles and documents

Hydroamination and hydroalkoxylation catalyzed by triflic acid. Parallels to reactions initiated with metal triflates

(Chemical Equation Presented) Intermolecular additions of the O-H bonds of phenols and alcohols and the N-H bonds of sulfonamides and benzamide to olefins catalyzed by 1 mol % of triflic acid and studies to define the relationship between these reactions and those catalyzed by metal triflates are reported. Cyclization of an alcohol containing pendant monosubstituted and trisubstituted olefins catalyzed by either triflic acid or metal triflates form products from addition to the more substituted olefin, and additions of tosylamide catalyzed by triflic acid or metal triflates form indistinguishable ratios of the two N-alkyl sulfonamides.

Iron(III) triflimide as a catalytic substitute for gold(I) in hydroaddition reactions to unsaturated carbon-carbon bonds

In this work it is shown that iron(III) and gold(I) triflimide efficiently catalyze the hydroaddition of a wide array of nucleophiles including water, alcohols, thiols, amines, alkynes, and alkenes to multiple C-C bonds. The study of the catalytic activity and selectivity of iron(III), gold(I), and Bronsted triflimides has unveiled that iron(III) triflimide [Fe(NTf 2)3] is a robust catalyst under heating conditions, whereas gold(I) triflimide, even stabilized by PPh3, readily decomposes at 80 °C and releases triflimidic acid (HNTf2) that can catalyze the corresponding reaction, as shown by in situ 19F, 15N, and 31P NMR spectroscopy. The results presented here demonstrate that each of the two catalyst types has weaknesses and strengths and complement each other. Iron(III) triflimide can act as a substitute of gold(I) triflimide as a catalyst for hydroaddition reactions to unsaturated carbon-carbon bonds. Lewis and Bronsted catalysis: It is shown that iron(III) catalyses as efficiently as gold(I) the hydroaddition of a wide array of nucleophiles, including water, alcohols, thiols, amines, alkynes, and alkenes, to multiple C-C bonds (see scheme). Copyright

Hidden Bronsted acid catalysis: Pathways of accidental or deliberate generation of triflic acid from metal triflates

The generation of a hidden Bronsted acid as a true catalytic species in hydroalkoxylation reactions from metal precatalysts has been clarified in case studies. The mechanism of triflic acid (CF3SO3H or HOTf) generation starting either from AgOTf in 1,2-dichloroethane (DCE) or from a Cp*RuCl2/AgOTf/phosphane combination in toluene has been elucidated. The deliberate and controlled generation of HOTf from AgOTf and cocatalytic amounts of tert-butyl chloride in the cold or from AgOTf in DCE at elevated temperatures results in a hidden Bronsted acid catalyst useful for mechanistic control experiments or for synthetic applications.

Process for Production of Carboxylic Acid Ester or Ether Compound

Disclosed is a process for production of a carboxylic acid ester from a carboxylic acid and an olefin or production of an ether compound from an alcohol and an olefin at low cost and with high yield in an industrially advantageous manner. The process comprises the step of reacting a carboxylic acid with an olefin to yield a corresponding carboxylic acid ester or reacting an alcohol with an olefin to yield a corresponding ether compound. In the process, a catalyst comprising a combination of (i) at least one metal compound selected from an iron compound, a cobalt compound and a nickel compound and (ii) an acidic compound is used.

Copper(II)-catalysed addition of O-H bonds to norbornene

Cu(OTf)2 is an inexpensive, air- and moisture-stable catalyst for the O-H addition of aliphatic and aromatic acids and alcohols to norbornene. The Royal Society of Chemistry 2005.

Effect of a substituent in the benzene ring upon the kinetics of acid-catalyzed hydrolysis of exo-2-norbornyl phenyl ether

The rate constants of hydrolysis for exo-2-norbornyl phenyl ether without substituent and with p-Me, p-Ac, m-CN, p-CN or p-NO2 group in the benzene ring were measured in concentrated perchloric acid solutions spectrophotometrically and/or by capillary GC. The effect of the substituent on the rate constants and other kinetic parameters of hydrolysis is small. The parameters are in agreement with the A-1 mechanism. The ether oxygen of the exo-epimer is much more basic than that of the endo-epimer (pKa,exo - pKa,endo ≈ 2), which causes a greater part of the exo/endo rate ratio than do the initial state energies and rate constants of the rate limiting stage, i.e. of the formation of the norbornyl cation and the substituted phenol. Acta Chemica Scandinavica 1997.

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.