Advanced search
1 file | 334.16 KB

Synthesis of 1-alkyl-2-(trifluoromethyl)azetidines and their regiospecific ring opening toward diverse α-(trifluoromethyl)amines via intermediate azetidinium salts

(2012) JOURNAL OF ORGANIC CHEMISTRY. 77(14). p.5982-5982
Author
Organization
Abstract
A convenient approach toward nonactivated 1-alkyl-2-(trifluoromethyl)azetidines as a new class of constrained azaheterocycles was developed staffing from ethyl 4,4,4-trifluoroacetoacetate via imination, hydride reduction, chlorination, and base-induced ring closure. Furthermore, the reactivity profile of these 2-CF3-azetidines was assessed by means of quaternization and subsequent regiospecific ring opening at C4 of the azetidinium intermediates by oxygen, nitrogen, carbon, sulfur, and halogen nucleophiles, pointing to a clear difference in reactivity compared to azetidines bearing other types of electron-withdrawing groups at C2.

Downloads

  • (...).docx
    • full text
    • |
    • UGent only
    • |
    • Word
    • |
    • 334.16 KB

Citation

Please use this url to cite or link to this publication:

Chicago
Kenis, Sara, Matthias D’hooghe, Guido Verniest, Anh Dang Thi Tuyet, Chinh Pham The, Tuyen Van Nguyen, and Norbert De Kimpe. 2012. “Synthesis of 1-alkyl-2-(trifluoromethyl)azetidines and Their Regiospecific Ring Opening Toward Diverse Α-(trifluoromethyl)amines via Intermediate Azetidinium Salts.” Journal of Organic Chemistry 77 (14): 5982–5982.
APA
Kenis, S., D’hooghe, M., Verniest, G., Tuyet, A. D. T., The, C. P., Nguyen, T. V., & De Kimpe, N. (2012). Synthesis of 1-alkyl-2-(trifluoromethyl)azetidines and their regiospecific ring opening toward diverse α-(trifluoromethyl)amines via intermediate azetidinium salts. JOURNAL OF ORGANIC CHEMISTRY, 77(14), 5982–5982.
Vancouver
1.
Kenis S, D’hooghe M, Verniest G, Tuyet ADT, The CP, Nguyen TV, et al. Synthesis of 1-alkyl-2-(trifluoromethyl)azetidines and their regiospecific ring opening toward diverse α-(trifluoromethyl)amines via intermediate azetidinium salts. JOURNAL OF ORGANIC CHEMISTRY. 2012;77(14):5982–5982.
MLA
Kenis, Sara, Matthias D’hooghe, Guido Verniest, et al. “Synthesis of 1-alkyl-2-(trifluoromethyl)azetidines and Their Regiospecific Ring Opening Toward Diverse Α-(trifluoromethyl)amines via Intermediate Azetidinium Salts.” JOURNAL OF ORGANIC CHEMISTRY 77.14 (2012): 5982–5982. Print.
@article{3097621,
  abstract     = {A convenient approach toward nonactivated 1-alkyl-2-(trifluoromethyl)azetidines as a new class of constrained azaheterocycles was developed staffing from ethyl 4,4,4-trifluoroacetoacetate via imination, hydride reduction, chlorination, and base-induced ring closure. Furthermore, the reactivity profile of these 2-CF3-azetidines was assessed by means of quaternization and subsequent regiospecific ring opening at C4 of the azetidinium intermediates by oxygen, nitrogen, carbon, sulfur, and halogen nucleophiles, pointing to a clear difference in reactivity compared to azetidines bearing other types of electron-withdrawing groups at C2.},
  author       = {Kenis, Sara and D'hooghe, Matthias and Verniest, Guido and Tuyet, Anh Dang Thi and The, Chinh Pham and Nguyen, Tuyen Van and De Kimpe, Norbert},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  language     = {eng},
  number       = {14},
  pages        = {5982--5982},
  title        = {Synthesis of 1-alkyl-2-(trifluoromethyl)azetidines and their regiospecific ring opening toward diverse \ensuremath{\alpha}-(trifluoromethyl)amines via intermediate azetidinium salts},
  url          = {http://dx.doi.org/10.1021/jo300694y},
  volume       = {77},
  year         = {2012},
}

Altmetric
View in Altmetric
Web of Science
Times cited: