Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 26, Pages 9252-9255Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja503830c
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Funding
- Department of Energy [DE-SC0005430]
- NSF [CHE-1306730]
- U.S. Department of Energy (DOE) [DE-SC0005430] Funding Source: U.S. Department of Energy (DOE)
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1306730] Funding Source: National Science Foundation
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The oxidative lactonization of N-substituted diethanolamines with the Pd catalyst [LPd-(OAc)](2)(2+)[OTf-](2) generates N-substituted morpholin-2-ones. The organocatalytic ring-opening polymerization of N-acyl morpholin-2-ones occurs readily to generate functionalized poly(aminoesters) with N-acylated amines in the polyester backbone. The thermodynamics of the ring-opening polymerization depends sensitively on the hybridization of the nitrogen of the heterocyclic lactone. N-Acyl morpholin-2-ones polymerize readily to generate polymorpholinones, but the N-aryl or N-alkyl substituted morpholin-2-ones do not polymerize. Experimental and theoretical studies reveal that the thermodynamics of ring opening correlates to the degree of pyramidalization of the endocydic N-atom. Deprotection of the poly(N-Bocmorpholin-2-one) yields a water-soluble, cationic polymorpholinone.
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