Functionalization and Linking Chemistry of Poly(styryl)lithium with 1,3‐Butadiene Diepoxide

AbstractSummary: The reaction of excess poly(styryl)lithium ($\overline M _{\rm n}$ = 1 400 g · mol−1) with 1,3‐butene diepoxide proceeds efficiently to produce a coupled product with two in‐chain hydroxyl groups. The pure coupled, functionalization product was isolated in quantitative yield by silica gel column chromatography. This product was characterized by 1H and 13C NMR spectroscopic analyses, as well as MALDI‐TOF mass spectrometry. The DEPT 13C NMR spectrum showed that a disecondary 1,2‐diol unit was present, consistent with attack of PSLi on the least‐substituted, methylene carbons of 1,3‐butadiene diepoxide. The MALDI‐TOF mass spectrum of the purified product exhibited only one distribution with monoisotopic peaks corresponding to the coupled, dihydroxy‐functionalized polystyrene.MALDI‐TOF mass spectrum of the purified, in‐chain, hydroxyl‐functionalized polystyrene and the reaction of PSLi with 1,3‐butadiene diepoxide.magnified imageMALDI‐TOF mass spectrum of the purified, in‐chain, hydroxyl‐functionalized polystyrene and the reaction of PSLi with 1,3‐butadiene diepoxide.