91840-84-5Relevant academic research and scientific papers
Synthesis of 2,5- and 2,6-Norbornane Derivatives with Prostaglandin-like Side Chains
Davies, David I.,Gomez, Peter M.,Hallett, Peter
, p. 843 - 848 (2007/10/02)
Norborn-5-en-2-endo-ylmethyl toluene-4-sulphonate, readily prepared from Diels-Alder adduct of cyclopentadiene and acrylic acid, has been converted, in six and seven stages respectively, into the prostaglandin-like compounds 2-endo-(6-carboxyhex-2-enyl)norbornan-5- and -6-exo-yl 2-hydroxyheptyl ethers.The synthesis of the former compounds involves a novel hydroxyethoxy mercuriation of a norbornene double bond.
Directionality of Proton Transfer in Solutions. Three Systems of Known Angularity
Menger, F. M.,Chow, J. F.,Kaiserman, H.,Vasquez, P. C.
, p. 4996 - 5002 (2007/10/02)
Three compounds were synthesized each possessing rigid carbon frameworks that hold an oxygen base near a mobile C-H proton in well-defined angular and distance relationships: 2-iodo-4-hydroxyindan, endo-5-hydroxybicycloheptan-2-one, and endo-2-hydroxy-exo-6-bromomethylheptane.Effective proton transfer was detected with the second and third compounds but not the first.The data suggest that C-to-O proton transfer with severely bent O/H/C angles (106 deg) is permissible if the O-H distance is less than the sum of the van der Waals radii. "Long distance" catalysis at active sites of enzymes appears unlikely.
