Photoinversion of sulfoxides as a source of diversity in dynamic combinatorial chemistry

Organic Letters

Volumn 13, Issue 1, 2011, Pages 142-145

  Di Stefano, Stefano ^a   Mazzonna, Marco ^a   Bodo, Enrico ^a   Mandolini, Luigi ^a   Lanzalunga, Osvaldo ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78650880683     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102715p     Document Type: Article

References (63)

1. Corbett, P. T.; Leclaire, J.; Vial, L.; West, K. R.; Wietor, J.-L.; Sanders, J. K. M.; Otto, S. Chem. Rev. 2006, 106, 3652-3711
2. Dynamic Combinatorial Chemistry; Reek, J. N. H.; Otto, S., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2010.
3. Brandli, C.; Ward, T. R. Helv. Chim. Acta 1998, 81, 1616-1621
4. Marsella, M. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1101-1103
5. Speller, S.; Nolte, R. J. M.; Rowan, A. E. Chem. Commun. 2005, 3535-3537
6. Leung, K. C.-F.; Aricó, F.; Cantrill, S. J.; Stoddart, J. F. J. Am. Chem. Soc. 2005, 127, 5808-5810
7. Storm, O.; Lüning, L. Chem.-Eur. J. 2002, 8, 793-798
8. Ziach, K.; Jurczak, J. Org. Lett. 2008, 10, 5158-5162
9. Giuseppone, N.; Lehn, J.-M. Chem.-Eur. J. 2006, 12, 1715-1722
10. Lam, R. T. S.; Belenguer, A.; Roberts, S. L.; Naumann, C.; Jarrosson, T.; Otto, S.; Sanders, J. K. M. Science 2005, 308, 667-669
11. Bulos, F.; Roberts, S. L.; Furlán, R. L. E.; Sanders, J. K. M. Org. Biomol. Chem. 2007, 5, 3092-3093
12. Voshell, S. M.; Lee, S. J.; Gagné, M. R. J. Am. Chem. Soc. 2006, 128, 12422-12423
13. Rowan, S. J.; Hamilton, D. G.; Brady, P. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1997, 119, 2578-2579
14. Rowan, S. J.; Brady, P. A.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2143-2145
15. Otto, S.; Furlan, R. L. E.; Sanders, J. K. M. Science 2002, 297, 590-593
16. Otto, S.; Kubik, S. J. Am. Chem. Soc. 2003, 125, 7804-7805
17. Corbett, P. T.; Tong, L. H.; Sanders, J. K. M.; Otto, S. J. Am. Chem. Soc. 2005, 127, 8902-8903
18. Leclaire, J.; Vial, L.; Otto, S.; Sanders, J. K. M. Chem. Commun. 2005, 1959-1961
19. Sarma, R. J.; Otto, S.; Nitschke, J. R. Chem.-Eur. J. 2007, 13, 9542-9546
20. Rodriguez-Docampo, Z.; Otto, S. Chem. Commun. 2008, 5301-5303
21. Fuchs, B.; Nelson, A.; Star, A.; Stoddart, J. F.; Vidal, S. Angew. Chem. 2003, 115, 4352-4356
22. Cacciapaglia, R.; Di Stefano, S.; Mandolini, L. J. Am. Chem. Soc. 2005, 127, 13666-13671
23. Di Stefano, S. J. Phys. Org. Chem. 2010, 23, 797-805
24. Berkovich-Berger, D.; Lemcoff, N. G. Chem. Commun. 2008, 1686-1688
25. For a previous example of PDCC, see: Ingerman, A. L.; Waters, M. L. J. Org. Chem. 2009, 74, 111-117 Here the azobenzene light-induced trans-cis inversion is used to interconvert the members of a dynamic library.
26. Pellissier, H. Tetrahedron 2006, 62, 5559-5601
27. Legros, J.; Dehli, J. R.; Bolm, C. Adv. Synth. Catal. 2005, 347, 19-31
28. Bentley, R. Chem. Soc. Rev. 2005, 34, 609-624
29. Fernandez, I.; Khiar, N. Chem. Rev. 2003, 103, 3651-3705
30. Carreno, M. C. Chem. Rev. 1995, 95, 1717-1760
31. Vos, B. W.; Jenks, W. S. J. Am. Chem. Soc. 2002, 124, 2544-2547
32. Lee, W.; Jenks, W. S. J. Org. Chem. 2001, 66, 474-480
33. Tsurutani, Y.; Machida, S.; Horie, K.; Kawashima, Y.; Nakano, H.; Hirao, K. J. Photochem. Photobiol. A:Chem. 1999, 122, 161-168
34. Guo, Y.; Jenks, W. S. J. Org. Chem. 1995, 60, 5480-5486
35. Mislow, K.; Axelrod, M.; Rayner, D. R.; Gotthardt, H.; Coyne, L. M.; Hammond, G. S. J. Am. Chem. Soc. 1965, 87, 4958-4960
36. Aurisicchio, C.; Baciocchi, E.; Gerini, M. F.; Lanzalunga, O. Org. Lett. 2007, 9, 1939-1942
37. Cooke, R. S.; Hammond, G. S. J. Am. Chem. Soc. 1970, 92, 2739-2745
38. Mislow, K.; Axelrod, M.; Rayner, D. R.; Gotthardt, H.; Coyne, L. M.; Cooke, R. S.; Hammond, G. S. J. Am. Chem. Soc. 1969, 92, 2739-2745
39. Cooke, R. S.; Hammond, G. S. J. Am. Chem. Soc. 1968, 90, 2958-2959
40. Spry, D. O. J. Am. Chem. Soc. 1970, 92, 5006-5008
41. Archer, R. A.; Kitchell, B. S. J. Am. Chem. Soc. 1966, 88, 3462-3463
42. Suwabe, S.; Okuhara, A.; Sugahara, T.; Suzuki, K.; Kunimasa, K.; Nakajima, T.; Kumafuji, Y.; Osawa, Y.; Yoshimura, T.; Morita, H. Tetrahedron Lett. 2009, 50, 1381-1384
43. Deubel, D. J. Org. Chem. 2001, 66, 2686-2691
44. Korang, J.; Grither, W. R.; McCulla, R. D. J. Am. Chem. Soc. 2010, 132, 4466-4476
45. McCulla, R. D.; Jenks, W. S. J. Am. Chem. Soc. 2004, 126, 16058-16065
46. Gregory, D. D.; Wan, Z. H.; Jenks, W. S. J. Am. Chem. Soc. 1997, 119, 94-102
47. Thomas, K. B.; Greer, A. J. Org. Chem. 2003, 68, 1886-1891
48. Mislow, K.; Schneider, P.; Ternay, A. L. J. Am. Chem. Soc. 1964, 86, 2957-2958
49. Acetonitrile was chosen because of its transparency in the UV spectral region investigated.
50. The photoinduced axial to equatorial S-O configuration change in 1,9-dithiaalkane-bridged thianthrene 10-oxides was accounted for in terms of the weak UV absorption of the axial isomer and the negligible absorption of the equatorial isomer (ref 13).
51. Bunce, N. J.; LaMarre, J.; Vaish, S. P. Photochem. Photobiol. 1984, 39, 531-533
52. Guo, Y.; Jenks, W. S. J. Org. Chem. 1997, 62, 857-864
53. T < 81 kcal/mol.
54. Jenks, W. S.; Lee, W.; Shutters, D. J. Phys. Chem. 1994, 98, 2282-2289
55. The evidence in favor of the existence of such mechanisms for photochemical isomerization that does not produce homolytic α-cleavage but involves a nonradiative decay from an exited state was discussed in detail by Jenks and co-workers (ref 10b). Although experimental evidence is accumulating, the precise details of the inversion mechanisms are still unknown. A pathway which is consistent with all of the experimental findings involves the following: (i) the initial formation of an electronically excited state in the pyramidal geometry, (ii) its geometric relaxation to a configuration which is approximately trigonal on sulfur, and (iii) a subsequent nonradiative decay to the ground state in a planar geometry (structurally similar to the thermal transition state) which evolves into one of the two possible configurations. The multiplicity of the excited state is still debated, although there is some evidence in favor of a singlet state as found in the present case.
56. 3CN at 280 nm.
57. 2 and both the thianthrene dioxide isomers does not seem allowed. Obviously, this interference increases when the concentration of the species to be titrated decreases.
58. Formation of complexes of tin ions with sulfoxides by interaction with the sulfinyl oxygen is well documented
59. Calligaris, M. Coord. Chem. Rev. 2004, 24, 8-351
60. Hsu, C. C.; Geanangel, R. A. Inorg. Chem. 1980, 19, 110-119 The structures of chelated complexes of disulfoxides with triphenyltin chloride with bonding occurring through the sulfinyl oxygen atoms have been also reported: Filgueiras, C. A. L.; Celso, C.; Marques, E. V.; Johnson, B. F. G. Inorg. Chim. Acta 1982, 59, 71-74
61. 2+ should justify qualitatively the preferential formation of cis-1.
62. 1/2 values have been reported.
63. Christinat, N.; Scopelliti, R.; Severin, K. Angew. Chem., Int Ed. 2008, 47, 1848-1852