Display options
Share it on

J Org Chem. 2006 Jan 06;71(1):341-4. doi: 10.1021/jo0513156.

Synthesis and characterization of norbornanediol isomers and their fluorinated analogues.

The Journal of organic chemistry

Scott M Grayson, Brian K Long, Shiro Kusomoto, Brian P Osborn, Ryan P Callahan, Charles R Chambers, C Grant Willson

Affiliations

  1. Department of Chemistry and Biochemistry, University of Texas, Austin, Texas 78712, USA.

PMID: 16388654 DOI: 10.1021/jo0513156

Abstract

[reaction: see text] 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.

Publication Types