Aromatic cation activation: Nucleophilic substitution of alcohols and carboxylic acids

Organic Letters

Volumn 16, Issue 6, 2014, Pages 1720-1723

  Nguyen, Thanh V ^a   Bekensir, Alp ^a  

^a CURTIN UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84896976431     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5003972     Document Type: Article

References (25)

1. Merling, G. Chem. Ber. 1981, 24, 3108
2. Doering, W.; von, E.; Knox, L. H. J. Am. Chem. Soc. 1954, 76, 3203
3. Hückel, E. Grundzüge der Theorie ungesättiger und aromatischer Verbindungen; Verlag Chem: Berlin, 1938; pp 77-85.
4. Sereda, O.; Tabassum, S.; Wilhelm, R. Top. Curr. Chem. 2010, 291, 349
5. Kelly, B. D.; Lambert, T. H. J. Am. Chem. Soc. 2009, 131, 13930
6. Hardee, D. J.; Kovalchuke, L.; Lambert, T. H. J. Am. Chem. Soc. 2010, 132, 5002
7. Srivastava, V. P.; Patel, R.; Garima; Yadav, L. D. S. Chem. Commun. 2010, 46, 5808
8. Vanos, C. M.; Lambert, T. H. Chem. Sci. 2010, 1, 705
9. Kelly, B. D.; Lambert, T. H. Org. Lett. 2011, 13, 740
10. Vanos, C. M.; Lambert, T. H. Angew. Chem., Int. Ed. 2011, 50, 12222
11. Bandar, J. S.; Lambert, T. H. J. Am. Chem. Soc. 2012, 134, 5552
12. Nacsa, E. D.; Lambert, T. H. Org. Lett. 2013, 15, 38
13. Bandar, J. S.; Lambert, T. H. Synthesis 2013, 45, 2485
14. Rai, A.; Yadav, L. D. S. Eur. J. Org. Chem. 2013, 1889
15. Bandar, J. S.; Lambert, T. H. J. Am. Chem. Soc. 2013, 135, 11799
16. Doering, W.; von, E.; Knox, L. H. J. Am. Chem. Soc. 1957, 79, 352
17. Parnes, Z. N.; Mur, G. D.; Kudryavtsev, R. V.; Kursanov, D. N. Dokl. Akad. Nauk SSSR 1964, 155, 1371
18. McGeachin, S. G. Can. J. Chem. 1969, 47, 151
19. Ritchie, C. D; Virtanen, P. O. I. J. Am. Chem. Soc. 1972, 94, 4963
20. Allen, J. M.; Lambert, T. H. J. Am. Chem. Soc. 2011, 133, 1260
21. Breslow, R. J. Am. Chem. Soc. 1957, 79, 5318
22. Aue, D. H. WIREs Comput. Mol. Sci. 2011, 1, 487
23. For NMR evidence of a similar equilibrium, see: Feigel, M.; Kessler, H. Tetrahedron 1976, 32, 1575
24. Denton, R. M.; An, J.; Adeniran, B. Chem. Commun. 2010, 46, 3025
25. Audi, G.; Bersillon, O.; Blachot, J.; Wapstra, A. H. Nucl. Phys. A 2003, 729, 3