482288-54-0

Basic information

• Product Name: Spiro[bicyclo[2.2.1]heptane-2,2-oxirane], 7,7-dimethyl-, (1R,2R,4R)- (9CI)
• Synonyms: Spiro[bicyclo[2.2.1]heptane-2,2-oxirane], 7,7-dimethyl-, (1R,2R,4R)- (9CI)
• CAS NO: 482288-54-0
• Molecular Formula: C10H16O
• Molecular Weight: 152.23344
• Product Categories: CYCLOPENTANE
• Mol File: 482288-54-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Spiro[bicyclo[2.2.1]heptane-2,2-oxirane], 7,7-dimethyl-, (1R,2R,4R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Spiro[bicyclo[2.2.1]heptane-2,2-oxirane], 7,7-dimethyl-, (1R,2R,4R)- (9CI)(482288-54-0)
• EPA Substance Registry System: Spiro[bicyclo[2.2.1]heptane-2,2-oxirane], 7,7-dimethyl-, (1R,2R,4R)- (9CI)(482288-54-0)

Safety Data

• Hazardous Substances Data: 482288-54-0(Hazardous Substances Data)

Upstream product

• 471-84-1 fenchene 
• 7378-37-2 α-fenchene 

Downstream Products

• 22425-99-6 2,7,7-trimethyl-exo-2-norbornyl p-nitrobenzoate 
• 22425-99-6 2,7,7-trimethyl-endo-2-norbornyl p-nitrobenzoate 

Relevant articles and documents

Acid-catalyzed reactions of camphene and α-fenchene epoxides

Isomerization of camphene and α-fenchene epoxides under homogeneous and heterogeneous conditions in media of various acidity was studied. The intermolecular reactions of these epoxy compounds with unsaturated aldehydes, allyl alcohol and methanol on askanite-bentonite clay yielded spiroacetals, and open-chain hydroxyethers and acetals. The results obtained are compared to those for reactions with the initial monoterpenes.

Structural Effects in Solvolytic Reactions. 49. Steric Effects as a Major Factor in the Exo:Endo Rate Ratios for the Solvolysis of 2,7,7-Trimethyl- and 2,6,6-Trimethyl-2-norbornyl p-Nitrobenzoates

The exo:endo rate ratio for solvolysis, in 80percent aqueous acetone at 25 deg C, decreases from 885 for 2-methyl-2-norbornyl p-nitrobenzoate to 6.1 for 2,7,7-trimethyl-2-norbornyl p-nitrobenzoate.On the other hand, it increases remarkably to 3 630 000 in the case of 2,6,6-trimethyl-2-norbornyl p-nitrobenzoate.These changes are clearly attributable to steric effects caused by the syn methyl group at the 7- and 6-positions, respectively.In the 2,7,7-trimethyl-2-norbornyl system, the very low exo:endo rate ratio arises primarily from an increased rate of solvolysis of the endo isomer, attributed to relief in steric strain, involving the syn 7-methyl and exo 2-methyl groups, during ionization.The extremely large exo:endo rate ratio in the 2,6,6-trimethyl-2-norbornyl system is attributed to the high rate of solvolysis of the exo isomer, caused by the relief in steric strain involving the endo 2-methyl and endo 6-methyl groups, as well as an especially slow rate for the endo isomer, caused by enhanced steric retardation of ionization.Thus, these results show clearly that exo:endo rate ratios can be strongly affected by steric effects in the rigid norbornyl system.