Allyl amines, polymerization, chain transfer

Transfer to monomer is of particular importance during the polymerization of allyl esters (113, X=()2CR), ethers (113, X=OR), amines (113, X=NR2) and related monomcrs.iw, 8, lb2 The allylic hydrogens of these monomers arc activated towards abstraction by both the double bond and the heteroatom substituent (Scheme 6.31). These groups lend stability to the radical formed (114) and are responsible for this radical adding monomer only slowly. This, in turn, increases the likelihood of side reactions (i.e. degradative chain transfer) and causes the allyl monomers to retard polymerization. 

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