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Synthesis and Characterization of Norbornanediol Isomers and Their Fluorinated Analogues

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journal contribution
posted on 06.01.2006, 00:00 by Scott M. Grayson, Brian K. Long, Shiro Kusomoto, Brian P. Osborn, Ryan P. Callahan, Charles R. Chambers, C. Grant Willson
Fluorinated norbornene monomers exhibit the requisite properties for inclusion in 157 nm photoresists, but traditional addition and radical polymerizations with these monomers have failed. Norbornanediols provide an alternate route to these materials via condensation polymerization, and methods have been developed for the efficient synthesis of the exo-2-syn-7- and endo-2-exo-3-dihydroxynorbornanes. Synthesis of the fluorinated analogues is complicated by steric and electronic effects; however, a high-yielding synthesis of endo-2-exo-3-dihydroxynorbornane bearing a 5-endo-[2,2-bis(trifluoromethyl)hydroxyethyl] substituent is reported.