Theoretical studies of ring-opening reactions of phenylcyclobutabenzenol and its reactions with alkynes catalyzed by rhodium complexes

Journal of Organic Chemistry

Volumn 78, Issue 22, 2013, Pages 11357-11365

  Li, Yang ^a   Lin, Zhenyang ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE INSERTIONS; CARBON ELIMINATIONS; DFT CALCULATION; INSERTION REACTIONS; RHODIUM COMPLEXES; RING OPENING REACTION; SITE SELECTIVITY; THEORETICAL STUDY;

CARBON; CATALYSIS; HYDROCARBONS; RHODIUM;

RHODIUM COMPOUNDS;

ALKYNE; BENZENE DERIVATIVE; PHENYLCYCLOBUTABENZENOL; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

ALCOHOLYSIS; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; RING OPENING; STEREOCHEMISTRY; THEORETICAL STUDY;

EID: 84887932053     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4019123     Document Type: Article

References (45)

1. Ruhland, K. Eur. J. Org. Chem. 2012, 2683
2. Seiser, T.; Saget, T.; Tran, D. N.; Cramer, N. Angew. Chem., Int. Ed. 2011, 50, 7740
3. Murakami, M.; Matsuda, T. Chem. Commun. 2011, 47, 1100
4. Park, Y. J.; Park, J.-W.; Jun, C. Acc. Chem. Res. 2008, 41, 222
5. Hang, X.; Chen, Q.; Xiao, J. J. Org. Chem. 2008, 73, 8598
6. Park, S.; Cha, J. K. Org. Lett. 2000, 2, 147
7. Ethirajan, M.; Oh, H.; Cha, J. K. Org. Lett. 2007, 9, 2693
8. Nishimura, T.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 2645
9. Ogata, K.; Shimada, D.; Furuya, S.; Fukuzawa, S. Org. Lett. 2013, 15, 1182
10. Sumida, Y.; Yorimitsu, H.; Oshima, K. Org. Lett. 2010, 12, 2254
11. Ghorai, M. K.; Shukla, D.; Bhattacharyya, A. J. Org. Chem. 2012, 77, 3740
12. Iwata, A.; Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2011, 76, 5506
13. Venkatasubbaiah, K.; Zhu, X.; Kays, E.; Hardcastle, K. I.; Jones, C. W. ACS Catal. 2011, 1, 489
14. Sawama, Y.; Sawama, Y.; Krause, N. Org. Lett. 2009, 11, 5034
15. Shi, M.; Liu, L.; Tang, J. Org. Lett. 2006, 8, 4043
16. Elsässer, B.; Schoenen, I.; Fels, G. ACS Catal. 2013, 3, 1397
17. Schalk, O.; Broman, S. L.; Petersen, M. Å.; Khakhulin, D. V.; Brogaard, R. Y.; Nielsen, M. B.; Boguslavskiy, A. E.; Stolow, A.; Sølling, T. I. J. Phys. Chem. A 2013, 117, 3340
18. Zhao, Z.; Moskaleva, L. V.; Rösch, N. ACS Catal. 2013, 3, 196
19. Ishida, M.; Sawano, S.; Masuda, Y.; Murakami, M. J. Am. Chem. Soc. 2012, 134, 17502
20. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
21. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200
22. Lee, C.; Yang, W.; Parr, G. Phys. Rev. B 1988, 37, 785
23. Stephens, P. J.; Devlin, F. J.; Chaobalowski, C. F. J. Phys. Chem. 1994, 98, 11623
24. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284
25. Hays, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299
26. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmenn, R.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111
27. Höllwarth, A.; Böhme, M.; Dapprich, S.; Ehlers, A. W.; Gobbi, A.; Jonas, V.; Köhler, K. F.; Stegmenn, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237
28. Fukui, K. J. Phys. Chem. 1970, 74, 4161
29. Fukui, K. Acc. Chem. Res. 1981, 14, 363
30. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669
31. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1966, 255, 327
32. Cossi, M.; Barone, V.; Mennucci, B.; Tomasi, J. Chem. Phys. Lett. 1988, 286, 253
33. Cossi, M.; Barone, V.; Robb, M. A. J. Chem. Phys. 1999, 111, 5295
34. Frisch, M. J.; Gaussian 09, revision D.01; Gaussian, Inc., Pittsburgh, PA, 2009.
35. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735
36. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. NBO 5.9; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 2011.
37. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157
38. Zhao, Y.; Truhlar, D. Theor. Chim. Acta 2008, 120, 215
39. Seiser, T.; Saget, T.; Tran, D. N.; Cramer, N. Angew. Chem., Int. Ed. 2011, 50, 7740
40. Bach, R. D.; Dmitrenko, O. J. Am. Chem. Soc. 2004, 126, 4444
41. Xue, L.; Ng, K, N.; Lin, Z. Dalton Trans. 2009, 5841
42. Margl, P.; Deng, L.; Ziegler, T. J. Am. Chem. Soc. 1998, 120, 5517
43. Niu, S.; Hall, M. B. Chem. Rev. 2000, 100, 353
44. Bai, T.; Zhu, J.; Xue, P.; Sung, H. H.-Y.; Williams, I. D.; Ma, S.; Lin, Z.; Jia, G. Organometallics 2007, 26, 5581
45. Li, Y.; Lin, Z. Organometallics 2013, 32, 3003