Palladium-mediated polymerization of cyclic diazoketones was investigated. Although cyclic diazoketones 1a,b derived from cyclohexanone and 1-tetralone did not homopolymerize, they can be used as a comonomer for copolymerization with polymerizable acyclic diazoketones. On the other hand, an alpha,beta-unsaturated cyclic diazoketone 2a prepared from 2-cyclohexen-1-one polymerized to give a polymer poly2a' with M-n = 1400 in a 23.8% yield. Addition of some nucleophiles to C=C bond in poly2a' was carried out. Copolymerization of 2a and its dimethyl-substituted analogues 2b,c with acyclic diazoketones was also investigated. (C) 2008 Wiley Periodicals, Inc.