An approach to 1,3,4-dioxaphospholane complexes through an acid-induced ring expansion of an oxaphosphirane complex: The problem of construction and deconstruction of O,P-heterocycles

Chemistry - An Asian Journal

Volumn 6, Issue 6, 2011, Pages 1539-1545

  Pérez, Janaina Marinas ^a   Helten, Holger ^b   Schnakenburg, Gregor ^a   Streubel, Rainer ^a  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

click chemistry; DFT calculations; epoxides; heterocycles; ring expansion

Indexed keywords

CLICK CHEMISTRY; DFT CALCULATION; EPOXIDES; HETEROCYCLES; RING EXPANSION;

ALDEHYDES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ASSOCIATION REACTIONS;

EID: 79957773105     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000861     Document Type: Article

References (43)

1. S. Bauer, A. Marinetti, L. Ricard, F. Mathey, Angew. Chem. 1990, 102, 1188-1189
2. Angew. Chem. Int. Ed. Engl. 1990, 29, 1166-1167.
3. R. Streubel, A. Kusenberg, J. Jeske, P. G. Jones, Angew. Chem. 1994, 106, 2564-2566
4. Angew. Chem. Int. Ed. Engl. 1994, 33, 2427-2428.
5. A. Özbolat, G. von Frantzius, J. M. Pérez, M. Nieger, R. Streubel, Angew. Chem. 2007, 119, 9488-9491
6. Angew. Chem. Int. Ed. 2007, 46, 9327-9330.
7. M. Bode, J. M. Pérez, G. Schnakenburg, J. Daniels, R. Streubel, Z. Anorg. Allg. Chem. 2009, 635, 8, 1163- 1171
8. C. Albrecht, J. M. Pérez, M. Bode, G. Schnakenburg, R. Streubel, Dalton Trans. 2011, 40, 2654-2665.
9. H. Helten, J. Marinas Pérez, J. Daniels, R. Streubel, Organometallics 2009, 28, 1221-1226.
10. For the term "click reaction," see:, H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075
11. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
12. J. Marinas Pérez, H. Helten, B. Donnadieu, C. A. Reed, R. Streubel, Angew. Chem. 2010, 122, 2670-2674
13. Angew. Chem. Int. Ed. 2010, 49, 2615-2618.
14. J. Marinas Pérez, C. Albrecht, H. Helten, G. Schnakenburg, R. Streubel, Chem. Commun. 2010, 46, 7244-7246.
15. 5-symmetrically substituted 1,3,4-dioxaphospholane complexes, see:, M. Bode, M. Nieger, R. Streubel, Organometallics 2007, 26, 245-246.
16. H. Helten, J. Daniels, M. Nieger, R. Streubel, New J. Chem. 2010, 34, 1593-1602.
17. This is in contrast to the case of N-protonated 1,3,4-oxazaphosphole complexes, in which a coupling between the N-H and the phosphorus atom was observed, see ref. [5]. Similar results were obtained for N-protonated 2H-1,4,2-diazaphosphole complexes:, H. Helten, M. Engeser, D. Gudat, R. Schilling, G. Schnakenburg, M. Nieger, R. Streubel, Chem. Eur. J. 2009, 15, 2602-2616.
18. Theoretical studies of the formation of O-protonated 1,3-dioxolanes predicted the possibility of a very fast (0.05 ps) ring-opening reaction. See:, A. Curioni, W. Andreoni, J. Hutter, H. Schiffer, M. Parrinello, J. Am. Chem. Soc. 1994, 116, 11251-11255.
19. Collect data collection software; B. V. Nonius, 1999.
20. Z. Otwinoski, W. Minor, Processing of X-ray Diffraction Data Collected in Oscillation Mode, Methods in Enzymology, Volume 276: Macromolecular Crystallography, Part A (Eds.:, C. W. Carter, Jr., R. M. Sweet,), Academic Press, New York, 1997, p. 307.
21. SHELXS-97:, G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467
22. G. M. Sheldrick, SHELXL-97, University of Göttingen, 1997.
23. R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-38.
24. R. Ahlrichs, M. Bär, M. Häser, H. Horn, C. Kölmel, Chem. Phys. Lett. 1989, 162, 165-169
25. M. von Arnim, R. Ahlrichs, J. Chem. Phys. 1999, 111, 9183-9190.
26. A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100.
27. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
28. K. Eichkorn, O. Treutler, H. Öhm, M. Häser, R. Ahlrichs, Chem. Phys. Lett. 1995, 240, 283-290
29. K. Eichkorn, O. Treutler, H. Öhm, M. Häser, R. Ahlrichs, Chem. Phys. Lett. 1995, 242, 652-660
30. K. Eichkorn, F. Weigend, O. Treutler, R. Ahlrichs, Theor. Chem. Acc. 1997, 97, 119-124.
31. A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571-2577.
32. D. Andrae, U. Häußermann, M. Dolg, H. Stoll, H. Preuß, Theor. Chim. Acta 1990, 77, 123-141.
33. A. Klamt, G. Schüürmann, J. Chem. Soc. Perkin Trans. 2 1993, 799-805.
34. A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
35. T. Helgaker, Chem. Phys. Lett. 1991, 182, 503-510.
36. P. Deglmann, F. Furche, R. Ahlrichs, Chem. Phys. Lett. 2002, 362, 511-518
37. P. Deglmann, F. Furche, J. Chem. Phys. 2002, 117, 9535-9538
38. P. Deglmann, K. May, F. Furche, R. Ahlrichs, Chem. Phys. Lett. 2004, 384, 103-107.
39. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
40. A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829-5835.
41. H. Helten, T. Schirmeister, B. Engels, J. Phys. Chem. A 2004, 108, 7691-7701
42. H. Helten, T. Schirmeister, B. Engels, J. Org. Chem. 2005, 70, 233-237
43. R. Vicik, H. Helten, T. Schirmeister, B. Engels, ChemMedChem 2006, 1, 1021-1028.