The DOI matches its Crossref record; 2 of the 2 references it cites were found in a registry or an index.
Cyclic Guanidine Organic Catalysts: What Is Magic About Triazabicyclodecene?
Abstract
The bicyclic guanidine 1,5,7- triazabicyclo[4.4.0]dec-5-ene (TBD) is an effective organocatalyst for the formation of amides from esters and primary amines. Mechanistic and kinetic investigations support a nucleophilic mechanism where TBD reacts reversibly with esters to generate an acyl-TBD intermediate that acylates amines to generate the amides. Comparative investigations of the analogous bicyclic guanidine 1,4,6-triazabicyclo[3.3.0]oct-4-ene (TBO) reveal it to be a much less active acylation catalyst than TBD. Theoretical and mechanistic studies imply that the higher reactivity of TBD is a consequence of both its higher basicity and nucleophilicity than TBO as well as the high reactivity of the acyl-TBD intermediate, which is sterically prevented from adopting a planar amide structure.
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Cites
Organocatalytic Ring-Opening Polymerization
Kamber, N. E., Jeong, W., Waymouth, R. M., Pratt, R. C., Lohmeijer, B. G. G., & Hedrick, J. L. (2007) · Chemical Reviews · doi:10.1021/cr068415b · Cited by 1,489
Self-citationPolymerization of Lactide with Zinc and Magnesium β-Diiminate Complexes: Stereocontrol and Mechanism
Chamberlain, B. M., Cheng, M., Moore, D. R., Ovitt, T. M., Lobkovsky, E. B., & Coates, G. W. (2001) · Journal of the American Chemical Society · doi:10.1021/ja003851f · Cited by 1,207
Cited by
Catalytic Control of the Vitrimer Glass Transition
Capelot, M., Unterlass, M. M., Tournilhac, F., & Leibler, L. (2012) · ACS Macro Letters · doi:10.1021/mz300239f · Cited by 1,206
Organocatalysis: Opportunities and Challenges for Polymer Synthesis
Kiesewetter, M. K., Shin, E. J., Hedrick, J. L., & Waymouth, R. M. (2010) · Macromolecules · doi:10.1021/ma9025948 · Cited by 907
Self-citationMennen, S. M., Alhambra, C., Allen, C. L., Barberis, M., Berritt, S., Brandt, T. A., Campbell, A. D., Castañón, J., Cherney, A. H., Christensen, M., et al. (2019) · Organic Process Research & Development · doi:10.1021/acs.oprd.9b00140 · Cited by 537
Fèvre, M., Pinaud, J., Gnanou, Y., Vignolle, J., & Taton, D. (2013) · Chemical Society Reviews · doi:10.1039/c2cs35383k · Cited by 532
Fast and selective ring-opening polymerizations by alkoxides and thioureas
Zhang, X., Jones, G. O., Hedrick, J. L., & Waymouth, R. M. (2016) · Nature Chemistry · doi:10.1038/nchem.2574 · Cited by 328
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Metadata
- Authors
- Kiesewetter, M. K., Scholten, M. D., Kirn, N., Weber, R. L., Hedrick, J. L., & Waymouth, R. M.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-11-23
- Volume
- 74
- Issue
- 24
- Pages
- 9490-9496
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2043821947
- Cited by
- 215
- References
- 2
- FWCI
- 5.59
- Type
- journal article
- Language
- en
- Open access
- closed
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