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Preparation and polymerization of the two isomeric (chloromethyl)oxetanes

Wicks, Douglas A. and Tirrell, David A. (1990) Preparation and polymerization of the two isomeric (chloromethyl)oxetanes. Journal of Polymer Science Part A: Polymer Chemistry, 28 (3). pp. 573-583. ISSN 0887-624X. https://resolver.caltech.edu/CaltechAUTHORS:WICjpsa1990

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/pola.1990.080280309DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/pola.1990.080280309/abstractPublisherArticle
ORCID:
AuthorORCID
Tirrell, David A.0000-0003-3175-4596
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.
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Issue or Number:3
Record Number:CaltechAUTHORS:WICjpsa1990
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:WICjpsa1990
Official Citation:Wicks, D. A. and Tirrell, D. A. (1990), Preparation and polymerization of the two isomeric (chloromethyl)oxetanes. J. Polym. Sci. A Polym. Chem., 28: 573–583. doi: 10.1002/pola.1990.080280309
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:53529
Collection:CaltechAUTHORS
Deposited By: Anne Hormann
Deposited On:22 Jan 2015 21:28
Last Modified:03 Oct 2019 07:50

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