Preparation and polymerization of the two isomeric (chloromethyl)oxetanes
- Creators
- Wicks, Douglas A.
-
Tirrell, David A.
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 CCl_4. 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.
Additional Information
Copyright © 1990 John Wiley & Sons, Inc. Received January 4, 1989; Accepted June 5, 1989. This work was supported by a Presidential Young Investigator Award of the National Science Foundation. NMR spectra were recorded in the University of Massachusetts NMR Laboratory, which is supported in part by the NSF Materials Research Laboratory at the University.Additional details
- Eprint ID
- 53529
- Resolver ID
- CaltechAUTHORS:WICjpsa1990
- NSF
- Created
-
2015-01-22Created from EPrint's datestamp field
- Updated
-
2021-11-10Created from EPrint's last_modified field