83679-37-2

Basic information

• Product Name: (+)-exo-Bicyclo-<2.2.1>-hepten-(5)-yl-(2)-acetat
• Synonyms: (+)-exo-Bicyclo-<2.2.1>-hepten-(5)-yl-(2)-acetat
• CAS NO: 83679-37-2
• Molecular Weight: 152.193
• Mol File: 83679-37-2.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (+)-exo-Bicyclo-<2.2.1>-hepten-(5)-yl-(2)-acetat(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-exo-Bicyclo-<2.2.1>-hepten-(5)-yl-(2)-acetat(83679-37-2)
• EPA Substance Registry System: (+)-exo-Bicyclo-<2.2.1>-hepten-(5)-yl-(2)-acetat(83679-37-2)

Safety Data

• Hazardous Substances Data: 83679-37-2(Hazardous Substances Data)

Upstream product

• 108-05-4 vinyl acetate 
• 542-92-7 cyclopenta-1,3-diene 
• 279-19-6 nortricyclane 
• 64-19-7 acetic acid 
• 694-98-4 norborn-5-en-2-one 
• 72150-05-1 Essigsaeure-<6exo-tosyloxy-2endo-norbornyl>ester 
• 72150-05-1 Essigsaeure<6endo-tosyloxy-2endo-norbornyl>ester 
• 694-97-3 endo-5-norbornen-2-ol 

Downstream Products

• 694-97-3 (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ol 
• 154278-40-7 (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate 
• 106928-44-3 (1R,2R,4R)-endo-bicyclo[2.2.1]hept-5-en-2-ol 
• 112836-09-6 (1R,2R,4R)-bicyclo[2.2.1]hept-5-en-2-yl acetate 
• 95475-09-5 2,2-dimethyl-endo-5-(3'-phenylsulphenylmethylbicyclo<2.2.1>hept-5'-en-2'-ylidene)-1,3-dioxan-4,6-dione 
• 95475-16-4 2,2-dimethyl-5-(3'-phenylsulfinylmethylbicyclo<2.2.1>hept-5'-en-2'-ylidene)-1,3-dioxan-4,6-dione 
• 95475-07-3 2,2-dimethyl-endo-5-(3'phenylthiomethylbicyclo<2.2.1>hept-5'-en-2'-ylidene)-1,3-dioxan-4,6-dione 
• 95475-07-3 2,2-dimethyl-exo-5-(3'-phenylthiomethylbicyclo<2.2.1>hept-5'-en-2'-ylidene)-1,3-dioxan-4,6-dione 
• 95475-19-7 2,2-dimethyl-5-(ξ-3'-phenylselenylbicyclo<2.2.1>hept-5'-en-2'-ylidene)-1,3-dioxan-4,6-dione 
• 95475-14-2 3-phenylsulfinylmethylbicyclo<2.2.1>hept-5-en-3-one 
• 95475-06-2 3-phenylthiomethylbicyclo<2.2.1>hept-5-en-2-one 
• 694-98-4 norborn-5-en-2-one 
• 476158-23-3 (5-exo,6-exo)-1,2,3,4-tetrahydro-1,4-methanophenazine-2,3-diyl dibenzoate 
• 737805-27-5 (5-exo,6-exo)-5,6-dibenzoyloxybicyclo[2.2.1]heptane-2,3-dione 

Relevant articles and documents

Gas-phase Diels-Alder cycloaddition reaction in the presence of methanol and water vapor

Hydrogen bonding effects of protic solvents, apart from bulk properties, on the reaction rate of the cycloaddition of cylopentadiene and vinyl acetate in the presence of water and methanol in the gas phase were investigated. The results showed that methan

Ring-opening metathesis - Cross-metathesis reactions (ROM-CM) of substituted norbornadienes and norbornenes

Ring-opening metathesis - cross-metathesis reactions (ROM-CM) of substituted norbornadienes and norbornenes were investigated. The reactions with symmetrical 2,3-disubstituted norbornadienes were found to be highly chemoselective, with the ROM reactions occurring only on the less substituted or less sterically hindered double bonds regardless of the electronic nature of the substituents, giving highly substituted cyclopentenes in moderate to good yields. This study provides an efficient method for the stereoselective synthesis of highly substituted cyclopentenoids. Long-range electronic effect of a remote substituent on unsymmetrical norbornenes in the ROM-CM reactions was also investigated. Low levels of regioselectivities were observed (50:50 to 69:31) with various remote substituents on the norbornenes.

Remote substituent effects on the oxymercuration of 2-substituted norbornenes: An experimental and theoretical study

The effect of a remote substituent on regioselectivity in the oxymercuration of 2-substituted norbornenes has been investigated experimentally and theoretically using density functional theory (DFT). Regioselectivities of 1:1 to 14:1 were observed with various 2-substituted norbornenes. Exo-2-substituted norbornenes always gave greater regioselectivities compared to the corresponding endo-2-substituted norbornenes. The effects of solvents on the regioselectivity have also been examined, and ethereal solvents were found to be the best choice giving the optimal yield and regioselectivity. The relative rate of oxymercuration was estimated by competition experiments. The least reactive substrate (X = OAc) gave the highest regioselectivity. According to DFT predictions, the increased difference between the reaction barriers that results in the greater regioselectivity is correlated directly with the larger polarity of the C=C double bond, which is attacked by the mercury and oxygen. A number of stable exo and endo conformers were predicted. All exo conformers show the same polarity of the double bond, while some endo conformers have a reversal of this polarity. All the conformers except those with the OAc substituent are very close in energy and thus should react. The existence of a mixture of endo conformers with the C=C double bond of opposite polarity clearly explains a decrease in regioselectivity for the endo species. The origin of the greatest regioselectivity for the OAc-2-norbornenes lies in the fact that the conformer with the largest polarity is notably lower in energy than others due to an internal C-H-O hydrogen bond.