154726-27-9

Upstream product

• 16626-39-4 5,5-dimethyl-1-vinylbicyclo[2.1.1]-hexane 
• 64-17-5 ethanol 
• 1004-46-2 (1S,4S)-5,5-Dimethyl-bicyclo[2.1.1]hexane-1-carbaldehyde 
• 7787-20-4 (1R)-fenchone 
• 4017-64-5 (1R,4R)-1-chloro-3,3-dimethyl-2-methylenebicyclo[2.2.1]heptane 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 10367-38-1 2-bromo-2-nitro-bornane 
• 6244-05-9 3,3-dimethyl-2-methylene-1-nitro-norbornane 
• 140147-15-5 (1R)-3,3-dimethyl-2-methylenenorborn-1-yl triflate 
• 154617-20-6 (-)-(1R)-3,3-dimethyl-2-oxo-1-norbornyl triflate 
• 154617-19-3 trifluoro-methanesulfonic acid (1R,4S)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl ester 
• 154726-31-5 trifluoro-methanesulfonic acid (1S,4S)-7,7-dimethyl-2-methylene-bicyclo[2.2.1]hept-1-yl ester 

Downstream Products

• 79635-05-5 6,6-Dimethylbicyclo<2.1.1>hexan-1-carbonsaeurechlorid 

Relevant academic research and scientific papers

Enantiospecific synthesis of substituted bicyclo[2.1.1]hexane-1-carboxylic acid and esters

The base promoted ring contraction of the readily accessible homochiral 2-oxo-1-norbornyl triflates 3 in 60% ethanol takes place with formation of bicyclo[2.1.1]hexane (4a), (+)- or (-)-7,7-dimethyl-bicyclo[2.1.1]hexan-1-carboxylic acids (4c or 4b) and the corresponding ethyl esters in good yields.

About the participation of σ, π and n orbitals in the solvolysis of 2- and 3-oxo-1-norbornyl triflates

The solvolysis of 3,3-dimethyl-2-oxo- and 2,2-dimethyl-3-oxo-1-norbornyltriflates (6 and 8) takes place with formation of ring contracted and fragmented products respectively. The effect of the substituents on the solvolysis rates is explained taking into account n- and σ-participation. This n,σ-participation causes changes in the structure and stability of the intermediate carbocations, which can be detected by the AM1 method.