Synthesis and Characterization of Norbornanediol Isomers and Their Fluorinated Analogues

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.