Resin effects in solid phase SNAr and SN2 macrocyclizations

Seven different supports were compared in solid-phase SNAr and S(N)2 macrocyclization reactions. Product purities were assayed for a relatively facile ring-closure process to give products 1 and 3. Some less-facile ring-closure reactions give the undesired dimeric macrocyclization by-products 2; some of these more-demanding ring closures were also examined. Finally, experiments were performed to gauge the rate of cyclizations on different resins, and some qualitative data were obtained for this. (C) 2000 John Wiley & Sons, Inc.