A tailor-made polymethacrylate bearing a pendant furfuryl group was prepared by atom transfer radical polymerization (ATRP), an important method of recent advances in controlled radical polymerization. It was otherwise difficult to prepare via conventional radical polymerization, because of several side reactions involving the reactive diene functionality of the furfuryl group. Successful Diels-Alder (DA) chemistry was carried out using this reactive furfuryl. group of the tailor-made polymer as diene and a bismaleimide as a dienophile. Interestingly, the resultant material was observed to be thermoreversible as evidenced by FT-IR and DSC studies. This example of application of a tailor-made polymer having controlled molecular architecture and with reactive diene functionality in DA chemistry will open new possibilities to prepare newer tailor-made reversible materials. (c) 2007 Wiley Periodicals, Inc.