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Model copolymerization reactions. Evidence against concerted complex addition in reactions of simple alkyl radicals with N-phenylmaleimide and donor olefins

Prementine, Glenn S. and Jones, Sharon A. and Tirrell, David A. (1989) Model copolymerization reactions. Evidence against concerted complex addition in reactions of simple alkyl radicals with N-phenylmaleimide and donor olefins. Macromolecules, 22 (2). pp. 770-775. ISSN 0024-9297. http://resolver.caltech.edu/CaltechAUTHORS:PREm1989b

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Abstract

Reductive demercuration was used to generate the 1-butyl and benzyl radicals in mixtures of N-phenylmaleimide (NPM) and either of the donor olefins styrene or 2-chloroethyl vinyl ether (CEVE). In each case, the major products of the reaction were derived from simple addition of the radical to NPM followed by transfer of a hydrogen atom to the initial adduct. Careful mass balances on NPM showed that mechanisms other than simple addition did not constitute important pathways for monomer consumption. These results argue against mechanistic schemes for radical copolymerization in which 1:l monomer complexes add in a concerted manner to growing macroradicals.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ma00192a043DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ma00192a043PublisherArticle
ORCID:
AuthorORCID
Tirrell, David A.0000-0003-3175-4596
Additional Information:© 1989 American Chemical Society. Received April 20, 1988. Acknowledgment is made to the donors of the Petroleum Research Fund, administered by the American Chemical Society, for partial support of this research. Support of our research programs by a Presidential Young Investigator Award of the National Science Foundation and by matching grants from Air Products and Chemicals Co., Chevron Research and Engineering Co., Exxon Research and Engineering Co., the General Electric Co., the Rohm and Haas Co., and Xerox Corp. are also acknowledged gratefully.
Funders:
Funding AgencyGrant Number
American Chemical Society Petroleum Research FundUNSPECIFIED
NSFUNSPECIFIED
Air Products and Chemicals Inc.UNSPECIFIED
Chevron Research and Engineering Co.UNSPECIFIED
Exxon Research and Engineering Co.UNSPECIFIED
General ElectricUNSPECIFIED
Rohm and Haas CompanyUNSPECIFIED
Xerox CorporationUNSPECIFIED
Record Number:CaltechAUTHORS:PREm1989b
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:PREm1989b
Official Citation:Model copolymerization reactions. Evidence against concerted complex addition in reactions of simple alkyl radicals with N-phenylmaleimide and donor olefins Glenn S. Prementine, Sharon A. Jones, and David A. Tirrell Macromolecules 1989 22 (2), 770-775
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:53534
Collection:CaltechAUTHORS
Deposited By: Anne Hormann
Deposited On:11 Jan 2015 03:25
Last Modified:11 Jan 2015 03:25

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