Breaking down the reactivity of λ3-iodanes: The impact of structure and bonding on competing reaction mechanisms

Journal of Organic Chemistry

Volumn 79, Issue 17, 2014, Pages 8374-8382

  Pinto De Magalhães, Halua ^a   Lüthi, Hans Peter ^a   Togni, Antonio ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; QUANTUM CHEMISTRY; SALTS; SYNTHESIS (CHEMICAL);

DIARYLIODONIUM SALTS; FUNCTIONALIZATIONS; HETEROCYCLIC MOIETIES; MECHANISTIC STUDIES; QUANTUM CHEMICAL CALCULATIONS; RADICAL MECHANISM; REACTION MECHANISM; REDUCTIVE ELIMINATION REACTION;

REACTION INTERMEDIATES;

DIARYLIODONIUM SALT; IODANE DERIVATIVE; IODINE; IODINE DERIVATIVE; ORGANOIODINE DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; CORRELATION ANALYSIS; COVALENT BOND; DECOMPOSITION; ELIMINATION REACTION; ENERGY TRANSFER; ISOMERIZATION; MOLECULE; QUANTUM CHEMISTRY; REACTION ANALYSIS; REDUCTION;

EID: 84924322550     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501714f     Document Type: Article

References (32)

1. Zhdankin, V. V. Hypervalent Iodine Chemistry: Preparation, Structure, and Synthetic Applications of Polyvalent Iodine Compounds; John Wiley & Sons: Chichester, UK, 2013.
2. Zhdankin, V. V.; Stang, P. Chem. Rev. 2008, 108, 5299-5358
3. Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
4. Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052-9070
5. Pinto de Magalhães, H.; Lüthi, H. P.; Togni, A. Org. Lett. 2012, 14, 3830-3833
6. Grushin, V. V. Chem. Soc. Rev. 2000, 29, 315-324
7. Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999.
8. Musher, J. Angew. Chem., Int. Ed. Engl. 1969, 8, 54-68
9. Ponec, R.; Duben, A. J. J. Comput. Chem. 1999, 20, 760-771
10. Ponec, R.; Yuzhakov, G.; Cooper, D. L. Theor. Chem. Acc. 2004, 112, 419-430
11. Woon, D. E.; Dunning, T. H., Jr. Comput. Theor. Chem. 2011, 963, 7-12
12. Moss, R. A.; Wilk, B.; Krogh-Jespersen, K.; Blair, J. T.; Westbrook, J. D. J. Am. Chem. Soc. 1989, 1, 250-258
13. Malmgren, J.; Santoro, S.; Jalalian, N.; Himo, F.; Olofsson, B. Chem.-Eur. J. 2013, 19, 10334-10342
14. Wang, B.; Graskemper, J. W.; Qin, L.; DiMagno, S. G. Angew. Chem., Int. Ed. 2010, 4079-4083
15. Frisch, M. J. Gaussian 09, Revision A.02; Gaussian Inc.: Wallingford, CT, 2009.
16. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO, version 3.1, 1988.
17. Becke, A. J. Chem. Phys. 1993, 5648-5652
18. Lee, C.; Yang, W.; Parr, R. Phys. Rev. B 1988, 785-789
19. Vosko, S.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 1200-1211
20. Stephens, P.; Devlin, F.; Chabalowski, C.; Frisch, M. J. Phys. Chem. 1994, 11623-11627
21. Dunning, T. J. Chem. Phys. 1989, 1007
22. Peterson, K. A.; Shepler, B. C.; Figgen, D.; Stoll, H. J. Phys. Chem. A 2006, 13877
23. Furche, F.; Ahlrichs, R. J. Chem. Phys. 2002, 117, 7433-7447
24. Scalmani, G.; Frisch, M. J.; Mennucci, B.; Tomasi, J.; Cammi, R.; Barone, V. J. Chem. Phys. 2006, 124, 094107
25. Caricato, M.; Mennucci, B.; Tomasi, J.; Ingrosso, F.; Cammi, R.; Corni, S.; Scalmani, G. J. Chem. Phys. 2006, 124520
26. Razskazovskii, Y. V.; Raiti, M. J.; Sevilla, M. D. J. Phys. Chem. A 1999, 103, 6351-6359
27. Bersuker, I. B. Chem. Rev. 2001, 101, 1067-114
28. Yang, D.-D.; Wang, F. Phys. Chem. Chem. Phys. 2012, 14, 15816-15825
29. Schwerdtfeger, P. J. Phys. Chem. 1996, 100, 2968-2973
30. Kim, H.; Choi, Y. J.; Lee, Y. S. J. Phys. Chem. B 2008, 112, 16021-16029
31. Bachler, V.; Halevi, E. A. Theor. Chim. Acta 1981, 59, 595-602
32. Falceto, A.; Casanova, D.; Alemany, P.; Alvarez, S. Inorg. Chem. 2013, 52, 6510-6519