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Abstract ω‐Formyl‐functionalized polystyrenes can be synthesized in quantitative yield by reacting poly(styryl)lithium (Mn = 2 × 103−8 × 103 g/mol) in benzene with a 0.1−0.4 molar excess of 4‐morpholinecarboxaldehyde followed by methanol termination and precipitation into methanol. Narrow molecular weight distribution ω‐formyl‐functionalized polystyrenes were characterized by hydroxylamine end‐group titration, thin layer chromatography and both 1H and 13C NMR spectroscopy. The mechanism of the functionalization was studied by trapping the tetrahedral α‐amino alkoxide intermediate with diphenylphosphinic chloride.
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Quirk et al. (1994) studied this question.
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