| Abstract: | 2-(Chloromethyl)oxetane was prepared in 8% overall yield from 2-propen-1-ol by protection of the alcohol with dihydropyran, epoxidation, ring expansion with dimethylsulfoxonium methylide, acid deprotection, and chlorination with triphenylphosphine in CCl4. 3-(Chloromethyl)oxetane was prepared in 22% overall yield by hydroboration-oxidation of 3-chloro-2-chloromethyl-1-propene followed by base-catalyzed cyclization. Each of the oxetanes was converted to the corresponding elastomeric homopolymer by treatment with a triethylaluminum–acetylacetone–water mixture. Poly[2-(chloromethyl)oxetane] was found to be similar to polyepichlorophydrin in reactivity toward benzoate ion, whereas poly[3-(chloromethyl)oxetane] is more reactive by a factor of 2. |
