Design of monomers for nonshrinking polymerizations,and synthesis of some N,S-analogs of spiroorthocarbonates

The design of spiroorthocarbonate monomers (SOCs) and related structures is discussed with the aim of maximizing monomer polymerizability in the absence of undesirable byproducts. The successful syntheses of N,S-analogs of aryl- and alkaryl-SOCs are reported; these are monomers of structure where P and Q are ? O? and ? OC(CH₃)₂?, mp 156–158°C; and P and Q are ? OCH₂? and ? OCH₂? , mp 148–150°C. As is indicated by infrared spectra, the polymerization of both monomers is initiated by boron trifluoride etherate. © 1993 John Wiley & Sons, Inc.