Theoretical investigation of the mechanisms and stereoselectivities of reductions of acyclic phosphine oxides and sulfides by chlorosilanes

Journal of Organic Chemistry

Volumn 77, Issue 8, 2012, Pages 3969-3977

  Krenske, Elizabeth H ^a,b  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROSILANES; COMPUTATIONAL STUDIES; NONIONIC; PHOSPHINE OXIDE; PHOSPHINE SULFIDE; REARRANGEMENT PATHWAYS; REARRANGEMENT PROCESS; THEORETICAL INVESTIGATIONS; TRANSITION STATE;

BENZENE; CHLORINE COMPOUNDS; PHOSPHORUS; SILICON; STEREOCHEMISTRY; STEREOSELECTIVITY; SULFUR COMPOUNDS;

PHOSPHORUS COMPOUNDS;

BENZENE; PHOSPHINE OXIDE DERIVATIVE; PHOSPHORANE DERIVATIVE; PHOSPHORUS; SILANE DERIVATIVE; SILICON; SULFIDE;

ARTICLE; HORNER REACTION; MATHEMATICAL COMPUTING; REDUCTION KINETICS; STEREOCHEMISTRY;

EID: 84860125921     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300346g     Document Type: Article

References (61)

1. Engel, R. In Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992; Chapter 5.
2. Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley: New York, 2000; pp 74-76.
3. Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411
4. Edmundson, R. S. E. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Chichester, 1992; Vol. 2; Chapter 7.
5. Gilheany, D. G.; Mitchell, C. M. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Chichester, 1990; Vol. 1, Chapter 7.
6. See also: Rajendran, K. V.; Gilheany, D. G. Chem. Commun. 2012, 48, 817-819 and references cited therein
7. 6 with retention of configuration were reported in: DeBruin, K. E.; Zon, G.; Naumann, K.; Mislow, K. J. Am. Chem. Soc. 1969, 91, 7027-7030
8. Krenske, E. H. J. Org. Chem. 2012, 77, 1-4
9. Horner, L.; Balzer, W. D. Tetrahedron Lett. 1965, 6, 1157-1162
10. Naumann, K.; Zon, G.; Mislow, K. J. Am. Chem. Soc. 1969, 91, 7012-7023
11. Zon, G.; DeBruin, K. E.; Naumann, K.; Mislow, K. J. Am. Chem. Soc. 1969, 91, 7023-7027
12. Naumann, K.; Zon, G.; Mislow, K. J. Am. Chem. Soc. 1969, 91, 2788-2789
13. Marsi, K. L. J. Am. Chem. Soc. 1969, 91, 4724-4729
14. Marsi, K. L. J. Org. Chem. 1974, 39, 265-267
15. Benkeser, R. A. Acc. Chem. Res. 1971, 4, 94-100
16. Urry, G. Acc. Chem. Res. 1970, 3, 306-312
17. Meyer-Wegner, F.; Nadj, A.; Bolte, M.; Auner, N.; Wagner, M.; Holthausen, M. C.; Lerner, H.-W. Chem.-Eur. J. 2011, 17, 4715-4719
18. Sirtl, E.; Reuschel, K. Z. Anorg. Allg. Chem. 1964, 332, 113-123
19. Nefedov, O. M.; Manakov, M. N. Angew. Chem., Int. Ed. 1966, 5, 1021-1038
20. Timms, P. L. Inorg. Chem. 1968, 7, 387-389
21. Atwell, W. H.; Weyenberg, D. R. Angew. Chem., Int. Ed. 1969, 8, 469-477
22. Chernyshev, E. A.; Komalenkova, N. G.; Bashkirova, S. A. J. Organomet. Chem. 1984, 271, 129-143
23. Chernyshev, E. A.; Komalenkova, N. G.; Bykovchenko, V. G. Russ. Chem. Bull. 1998, 47, 1029-1036
24. Walker, K. L.; Jardine, R. E.; Ring, M. A.; O'Neal, H. E. Int. J. Chem. Kinet. 1998, 30, 69-88
25. Karsch, H. H.; Schlüter, P. A.; Bienlein, F.; Herker, M.; Witt, E.; Sladek, A.; Heckel, M. Z. Anorg. Allg. Chem. 1998, 624, 295-309
26. Kang, S.-H.; Han, J. S.; Lee, M. E.; Yoo, B. R.; Jung, I. N. Organometallics 2003, 22, 2551-2553
27. Ghadwal, R. S.; Roesky, H. W.; Merkel, S.; Henn, J.; Stalke, D. Angew. Chem., Int. Ed. 2009, 48, 5683-5686
28. Ghadwal, R. S.; Roesky, H. W.; Merkel, S.; Stalke, D. Chem.-Eur. J. 2010, 16, 85-88
29. Ghadwal, R. S.; Pröpper, K.; Dittrich, B.; Jones, P. G.; Roesky, H. W. Inorg. Chem. 2011, 50, 358-364
30. Wang, Y.; Xie, Y.; Wei, P.; King, R. B.; Schaefer, H. F., III; Schleyer, P. v. R.; Robinson, G. H. Science 2008, 321, 1069-1071
31. Gillette, G. R.; Noren, G. H.; West, R. Organometallics 1989, 8, 487-491
32. Belzner, J.; Ihmels, H. Adv. Organomet. Chem. 1998, 43, 1-42
33. Bharatam, P. V.; Moudgil, R.; Kaur, D. Organometallics 2002, 21, 3683-3690
34. Takeda, N.; Kajiwara, T.; Suzuki, H.; Okazaki, R.; Tokitoh, N. Chem.-Eur. J. 2003, 9, 3530-3543
35. 3), see: du Mont, W.-W.; Gust, T.; Seppälä, E.; Wismach, C. J. Organomet. Chem. 2004, 689, 1331-1336
36. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision E.01, Gaussian, Inc., Wallingford, CT, 2004.
37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford, CT, 2009.
38. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
39. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377
40. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
41. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161
42. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527
43. Grimme, S. J. Chem. Phys. 2003, 118, 9095-9102
44. Gerenkamp, M.; Grimme, S. Chem. Phys. Lett. 2004, 392, 229-235
45. Grimme, S. J. Phys. Chem. A 2005, 109, 3067-3077
46. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995-2001
47. Barone, V.; Cossi, M.; Tomasi, J. J. Comput. Chem. 1998, 19, 404-417
48. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
49. Legault, C. Y., CYLview, 1.0b, Université de Sherbrooke, 2009, (http://www.cylview.org).
50. 2, were reported by Kutzelnigg and Wasilewski: Kutzelnigg, W.; Wasilewski, J. J. Am. Chem. Soc. 1982, 104, 953-960
51. Wu, H.-C.; Yu, J.-Q.; Spencer, J. B. Org. Lett. 2004, 6, 4675-4678
52. Wang, P.; Agrafiotis, D. K.; Streitwieser, A.; Schleyer, P. v. R. J. Chem. Soc., Chem. Commun. 1990, 201-203
53. Wasada, H.; Hirao, K. J. Am. Chem. Soc. 1992, 114, 16-27
54. Gounev, T. K.; Durig, J. R. Chem. Phys. 1996, 205, 109-126
55. López, C. S.; Faza, O. N.; de Lera, A. R.; York, D. M. Chem.-Eur. J. 2005, 11, 2081-2093
56. Couzijn, E. P. A; Slootweg, J. C.; Ehlers, A. W.; Lammertsma, K. J. Am. Chem. Soc. 2010, 132, 18127-18140
57. 2 forms stronger donor-acceptor complexes with harder donors: Oláh, J.; De Proft, F.; Veszprémi, T.; Geerlings, P. J. Phys. Chem. A 2005, 109, 1608-1615
58. Cai, Y.; Roberts, B. P. Tetrahedron Lett. 2001, 42, 4581-4584
59. Romeo, R.; Wozniak, L. A.; Chatgilialoglu, C. Tetrahedron Lett. 2000, 41, 9899-9902
60. 4/ hydrosiloxane: Petit, C.; Favre-Reguillon, A.; Albela, B.; Bonneviot, L.; Mignani, G.; Lemaire, M. Organometallics 2009, 28, 6379-6382
61. Quin, L. D.; Caster, K. C.; Kisalus, J. C.; Mesch, K. A. J. Am. Chem. Soc. 1984, 106, 7021-7032