Three adamantane derivatives Substituted by epoxy groups, 1,3-bis(glycidyloxy)adamantane (2a), 5,7-dimethyl-1,3-bis(glycidyloxy)adamantane (2b), 1,3,5-tris(glycidyloxy)adamantane (2c), were synthesized from the corresponding adamantanediol or triol in good yields. These three epoxy compounds were polymerized with in acid anhydride and the heat resistance of & resulting resins was evaluated. The resin prepared from 2c exhibited high heat resistance with the glass transition temperature (T,) of 208 degrees C and low degree of coloring by heating. The epoxy compounds, were also found to be potentially useful as the precursors of high heat-resistant resins by thermal homopolymerization. (c) 2009 Wiley Periodicals, Inc. J Appl Polym Sci 112: 496-504, 2009