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- W2094981421 abstract "2,6-Dioxabicyclo[2.2.1]heptane (3), the parent of a new ring system, has been synthesized by acid-catalyzed bicyclization of 1,1-diethoxy-3-hydroxymethyl-4-butanol. Conditions which were crucial to success included working in dilute dioctyl phthalate under high vacuum with vigorous stirring and distilling 3 as formed.2,7-Dioxabicyclo[2.2.1]heptane (4) was synthesized by similar acid-catalyzed cyclization of either 5-hydroxy-2-methoxytetrahydropyran or 1,1-diethoxy-4,5-pentanediol.In acid-catalyzed hydrolysis, 3 was almost one million times as reactive as dimethyl acetal, and 4 was only slightly less. General acid catalysis was observed for both during studies of hydrolysis in presence of buffers.Polymerization of 3 occurred very readily with a variety of cationic initiators. Protonic acids gave high conversion to soluble polymer which was of moderate molecular weight (ζinh = 0.35), liquid (rubber), and consisted of a 60:40 mixture of isomers (probably trans:cis) detected by NMR.Cationic polymerization of 4 also occurred readily. Again, high conversions to moderate molecular weight liquid polymer were obtained. At −78°C, the polymer contained exclusively tetrahydrofuran links; at a higher temperature, several initiators gave significant amounts of tetrahydropyran links." @default.
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- W2094981421 date "2007-03-08" @default.
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- W2094981421 title "Synthesis, hydrolytic reactivity, and polymerization of 2,6- and 2,7-dioxabicyclo[2.2.1]-heptanes" @default.
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- W2094981421 doi "https://doi.org/10.1002/polc.5070560112" @default.
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