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The elusive seven-membered cyclic imino ether tetrahydrooxazepine

Bart Verbraeken (UGent) , Jan Hullaert (UGent) , Joachim Van Guyse (UGent) , Kristof Van Hecke (UGent) , Johan Winne (UGent) and Richard Hoogenboom (UGent)
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Abstract
Cyclic imino ether heterocycles are used as ligands in transition metal catalysis, in various drugs and as reactive monomers in living cationic ring-opening polymerization (CROP). While five- and six-membered cyclic imino ethers, i.e. 2-oxazolines and 4,S-dihydro-1,3-oxazines, have extensively been studied in these areas, their seven-membered ring counterparts have remained unexplored. Herein, we report the synthesis of 2-phenyl-4,5,6,7-tetrahydro-1,3-oxazepine allowing reassignment of the earlier, incorrectly reported 4,5,6,7-tetrahydro-1,3-oxazepines as their N-acylated pyrrolidine isomers. Finally, we also report a comparison of the CROP reactivity of a homologous series of cyclic imino ethers with a 2-carbon, 3-carbon, and 4-carbon methylene bridge, revealing a remarkable ring size effect.
Keywords
IMIDATE SALTS, POLYMERIZATION, HYDROLYSIS, 2-OXAZOLINES, HETEROCYCLES, 1_3-OXAZINE, ADDITIONS, CLEAVAGE, ACIDS

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Chicago
Verbraeken, Bart, Jan Hullaert, Joachim Van Guyse, Kristof Van Hecke, Johan Winne, and Richard Hoogenboom. 2018. “The Elusive Seven-membered Cyclic Imino Ether Tetrahydrooxazepine.” Journal of the American Chemical Society 140 (50): 17404–17408.
APA
Verbraeken, B., Hullaert, J., Van Guyse, J., Van Hecke, K., Winne, J., & Hoogenboom, R. (2018). The elusive seven-membered cyclic imino ether tetrahydrooxazepine. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 140(50), 17404–17408.
Vancouver
1.
Verbraeken B, Hullaert J, Van Guyse J, Van Hecke K, Winne J, Hoogenboom R. The elusive seven-membered cyclic imino ether tetrahydrooxazepine. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. 2018;140(50):17404–8.
MLA
Verbraeken, Bart et al. “The Elusive Seven-membered Cyclic Imino Ether Tetrahydrooxazepine.” JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 140.50 (2018): 17404–17408. Print.
@article{8600139,
  abstract     = {Cyclic imino ether heterocycles are used as ligands in transition metal catalysis, in various drugs and as reactive monomers in living cationic ring-opening polymerization (CROP). While five- and six-membered cyclic imino ethers, i.e. 2-oxazolines and 4,S-dihydro-1,3-oxazines, have extensively been studied in these areas, their seven-membered ring counterparts have remained unexplored. Herein, we report the synthesis of 2-phenyl-4,5,6,7-tetrahydro-1,3-oxazepine allowing reassignment of the earlier, incorrectly reported 4,5,6,7-tetrahydro-1,3-oxazepines as their N-acylated pyrrolidine isomers. Finally, we also report a comparison of the CROP reactivity of a homologous series of cyclic imino ethers with a 2-carbon, 3-carbon, and 4-carbon methylene bridge, revealing a remarkable ring size effect.},
  author       = {Verbraeken, Bart and Hullaert, Jan and Van Guyse, Joachim and Van Hecke, Kristof and Winne, Johan and Hoogenboom, Richard},
  issn         = {0002-7863},
  journal      = {JOURNAL OF THE AMERICAN CHEMICAL SOCIETY},
  keywords     = {IMIDATE SALTS,POLYMERIZATION,HYDROLYSIS,2-OXAZOLINES,HETEROCYCLES,1_3-OXAZINE,ADDITIONS,CLEAVAGE,ACIDS},
  language     = {eng},
  number       = {50},
  pages        = {17404--17408},
  title        = {The elusive seven-membered cyclic imino ether tetrahydrooxazepine},
  url          = {http://dx.doi.org/10.1021/jacs.8b10918},
  volume       = {140},
  year         = {2018},
}

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