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Triazolinediones as highly enabling synthetic tools

Kevin De Bruycker (UGent) , Stijn Billiet (UGent) , Hannes Houck (UGent) , Subrata Chattopadhyay (UGent) , Johan Winne (UGent) and Filip Du Prez (UGent)
(2016) CHEMICAL REVIEWS. 116(6). p.3919-3974
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Abstract
Triazolinediones (TADs) are unique reagents in organic synthesis that have also found wide applications in different research disciplines, in spite of their somewhat "exotic" reputation. In this review, we offer two case studies that demonstrate the possibilities of these versatile and reliable synthetic tools, namely, in the field of polymer science as well as in more recently emerging applications in the field of click chemistry. As the general use of triazolinediones has always been hampered by the limited commercial and synthetic availability of such reagents, we also offer a review of the available TAD reagents, together with a detailed discussion of their synthesis and reactivity. This review thus aims to serve as a practical guide for researchers that are interested in exploiting and further developing the exceptional click -like reactivity of triazolinediones in various applications.
Keywords
DIELS-ALDER REACTION, PERFORMANCE LIQUID-CHROMATOGRAPHY, ELECTROPHILIC, AROMATIC-SUBSTITUTION, SOLVENT-FREE CONDITIONS, COOPERATIVE STRUCTURE, FORMATION, TANDEM MASS-SPECTROMETRY, SILICA SULFURIC-ACID, IN-SITU, GENERATION, LOW-TEMPERATURE MODIFICATION, ASSOCIATION CHAIN POLYMERS

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Chicago
De Bruycker, Kevin, Stijn Billiet, Hannes Houck, Subrata Chattopadhyay, Johan Winne, and Filip Du Prez. 2016. “Triazolinediones as Highly Enabling Synthetic Tools.” Chemical Reviews 116 (6): 3919–3974.
APA
De Bruycker, K., Billiet, S., Houck, H., Chattopadhyay, S., Winne, J., & Du Prez, F. (2016). Triazolinediones as highly enabling synthetic tools. CHEMICAL REVIEWS, 116(6), 3919–3974.
Vancouver
1.
De Bruycker K, Billiet S, Houck H, Chattopadhyay S, Winne J, Du Prez F. Triazolinediones as highly enabling synthetic tools. CHEMICAL REVIEWS. 2016;116(6):3919–74.
MLA
De Bruycker, Kevin, Stijn Billiet, Hannes Houck, et al. “Triazolinediones as Highly Enabling Synthetic Tools.” CHEMICAL REVIEWS 116.6 (2016): 3919–3974. Print.
@article{8502315,
  abstract     = {Triazolinediones (TADs) are unique reagents in organic synthesis that have also found wide applications in different research disciplines, in spite of their somewhat {\textacutedbl}exotic{\textacutedbl} reputation. In this review, we offer two case studies that demonstrate the possibilities of these versatile and reliable synthetic tools, namely, in the field of polymer science as well as in more recently emerging applications in the field of click chemistry. As the general use of triazolinediones has always been hampered by the limited commercial and synthetic availability of such reagents, we also offer a review of the available TAD reagents, together with a detailed discussion of their synthesis and reactivity. This review thus aims to serve as a practical guide for researchers that are interested in exploiting and further developing the exceptional click -like reactivity of triazolinediones in various applications.},
  author       = {De Bruycker, Kevin and Billiet, Stijn and Houck, Hannes and Chattopadhyay, Subrata and Winne, Johan and Du Prez, Filip},
  issn         = {0009-2665},
  journal      = {CHEMICAL REVIEWS},
  keyword      = {DIELS-ALDER REACTION,PERFORMANCE LIQUID-CHROMATOGRAPHY,ELECTROPHILIC,AROMATIC-SUBSTITUTION,SOLVENT-FREE CONDITIONS,COOPERATIVE STRUCTURE,FORMATION,TANDEM MASS-SPECTROMETRY,SILICA SULFURIC-ACID,IN-SITU,GENERATION,LOW-TEMPERATURE MODIFICATION,ASSOCIATION CHAIN POLYMERS},
  language     = {eng},
  number       = {6},
  pages        = {3919--3974},
  title        = {Triazolinediones as highly enabling synthetic tools},
  url          = {http://dx.doi.org/10.1021/acs.chemrev.5b00499},
  volume       = {116},
  year         = {2016},
}

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