Single enantiomer 2-hydroxy-3-butenyl tosylate is a key precursor for single enantiomer 3,4-epoxy-1-butene and 3-butene-1,2-diol. The epoxide results from ring-closure of the hydroxytosylate while the diol is obtained through the intermediacy of the corresponding cyclic carbonate. This latter sequence avoids the loss of enantiomeric purity observed through direct hydrolysis.
The photopolymerization of 3,4-epoxy-1-butene (1) was investigated using Fourier transform real-time infrared spectroscopy. The effects of photoinitiator structure and concentration and light intensity on the photopolymerization were investigated. Monomer 1 was found to be more reactive than its saturated analog, 1,2-epoxybutene, and its halogenated derivatives, 3,4-dibromo-1,2-epoxybutane and 3,4-dichloro-1,2-epoxybutane.
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