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Endo and Exo Diels-Alder Adducts: Temperature-Tunable Building Blocks for Selective Chemical Functionalization

Overview
Journal J Am Chem Soc
Specialty Chemistry
Date 2018 Apr 4
PMID 29613783
Citations 16
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Abstract

The development and application of a novel endo furan-protected maleimide building block is reported. The endo isomer undergoes deprotection at temperatures ∼50 °C below the exo derivative. This enables a simple and powerful approach to quantitatively and selectively introduce functional maleimide groups via temperature modulation.

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References
1.
Barker I, Hall D, Hansell C, Du Prez F, OReilly R, Dove A . Tetrazine-norbornene click reactions to functionalize degradable polymers derived from lactide. Macromol Rapid Commun. 2015; 32(17):1362-6. DOI: 10.1002/marc.201100324. View

2.
Lee I, Discekici E, Shankel S, Anastasaki A, Read de Alaniz J, Hawker C . Desulfurization-bromination: direct chain-end modification of RAFT polymers. Polym Chem. 2018; 8(46):7188-7194. PMC: 6201749. DOI: 10.1039/C7PY01702B. View

3.
Paulohrl T, Inglis A, Barner-Kowollik C . Reversible Diels-Alder chemistry as a modular polymeric color switch. Adv Mater. 2010; 22(25):2788-91. DOI: 10.1002/adma.201000361. View

4.
Pearson R, Lim C, McCarthy B, Musgrave C, Miyake G . Organocatalyzed Atom Transfer Radical Polymerization Using N-Aryl Phenoxazines as Photoredox Catalysts. J Am Chem Soc. 2016; 138(35):11399-407. PMC: 5485656. DOI: 10.1021/jacs.6b08068. View

5.
Pan X, Fang C, Fantin M, Malhotra N, So W, Peteanu L . Mechanism of Photoinduced Metal-Free Atom Transfer Radical Polymerization: Experimental and Computational Studies. J Am Chem Soc. 2016; 138(7):2411-25. DOI: 10.1021/jacs.5b13455. View