Macromolecules, volume 48, issue 6, pages 1679-1687
Dramatic Behavioral Differences of the Copolymerization Reactions of 1,4-Cyclohexadiene and 1,3-Cyclohexadiene Oxides with Carbon Dioxide
Publication type: Journal Article
Publication date: 2015-03-05
Materials Chemistry
Organic Chemistry
Inorganic Chemistry
Polymers and Plastics
Abstract
The copolymerization of 1,3-cyclohexadiene oxide (1,2-epoxy-3-cyclohexene) with CO2 in the presence of the binary catalyst (salen)CoX or (salen)CrX and onium salts was shown to selectively afford the completely alternating copolymer poly(1,3-cyclohexadiene carbonate) in good yield. In the process catalyzed by the cobalt(III) system, the reaction was 100% selective for copolymer, whereas employing the higher temperature chromium(III) catalyst, the reaction yielded in addition to copolymer a significant quantity of the cis-1,3-cyclohexadiene carbonate. Importantly, no corresponding trans-1,3-cyclohexadiene carbonate was produced. The reactivity of 1,3-cyclohexadiene oxide in coupling reactions with CO2 was strikingly greater than that of 1,4-cyclohexadiene oxide under either catalytic conditions. Authentic samples of the cis-cyclic carbonate and trans-cyclic carbonate were synthesized from epoxide and CO2 using ZnCl2/PPNI catalyzed and trans-diol/ethyl chloroformate routes, respectively. trans-1,3-Cyclohexa...
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Darensbourg D. J. et al. Dramatic Behavioral Differences of the Copolymerization Reactions of 1,4-Cyclohexadiene and 1,3-Cyclohexadiene Oxides with Carbon Dioxide // Macromolecules. 2015. Vol. 48. No. 6. pp. 1679-1687.
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Darensbourg D. J., Chung W. C., Yeung A. D., Luna M. Dramatic Behavioral Differences of the Copolymerization Reactions of 1,4-Cyclohexadiene and 1,3-Cyclohexadiene Oxides with Carbon Dioxide // Macromolecules. 2015. Vol. 48. No. 6. pp. 1679-1687.
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TY - JOUR
DO - 10.1021/acs.macromol.5b00172
UR - https://doi.org/10.1021/acs.macromol.5b00172
TI - Dramatic Behavioral Differences of the Copolymerization Reactions of 1,4-Cyclohexadiene and 1,3-Cyclohexadiene Oxides with Carbon Dioxide
T2 - Macromolecules
AU - Darensbourg, Donald J.
AU - Chung, Wan Chun
AU - Yeung, A D
AU - Luna, Mireya
PY - 2015
DA - 2015/03/05
PB - American Chemical Society (ACS)
SP - 1679-1687
IS - 6
VL - 48
SN - 0024-9297
SN - 1520-5835
ER -
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@article{2015_Darensbourg,
author = {Donald J. Darensbourg and Wan Chun Chung and A D Yeung and Mireya Luna},
title = {Dramatic Behavioral Differences of the Copolymerization Reactions of 1,4-Cyclohexadiene and 1,3-Cyclohexadiene Oxides with Carbon Dioxide},
journal = {Macromolecules},
year = {2015},
volume = {48},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.macromol.5b00172},
number = {6},
pages = {1679--1687},
doi = {10.1021/acs.macromol.5b00172}
}
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Darensbourg, Donald J., et al. “Dramatic Behavioral Differences of the Copolymerization Reactions of 1,4-Cyclohexadiene and 1,3-Cyclohexadiene Oxides with Carbon Dioxide.” Macromolecules, vol. 48, no. 6, Mar. 2015, pp. 1679-1687. https://doi.org/10.1021/acs.macromol.5b00172.