1,1,9,9-Tetrafluoro[2.2]paracyclophane (1) was prepared successfully as white crystals in 72% yield via two-step reactions from 1,9-diketo[2.2]-paracyclophane. The polymerization of 1 by the vapor deposition method was carried out at pyrolysis temperature range of 400 to 800 degrees C and deposition temperature range of -20 to 20 degrees C, and a tough, transparent poly(alpha,alpha-difluoro-p-xylylene) film was obtained in 72% yield at the pyrolysis temperature of 750 degrees C and the deposition temperature of -20 degrees C. It was found that the pyrolysis of 1 gave a reactive alpha,alpha-difluoro-p-xylylene, which polymerized on the head-to-tail addition to give poly(alpha,alpha-difluoro-p-xylylene). Some properties such as solubility, thermal stability, glass transition temperature, and density for poly(alpha,alpha-difluoro-p-xylylene) were studied.