Thioformaldehyde S-methylide and thioacetone S-methylide: An ab initio MO study of structure and cycloaddition reactivity

Chemistry - A European Journal

Volumn 9, Issue 10, 2003, Pages 2245-2255

  Sustmann, Reiner ^a   Sicking, Willi ^a   Huisgen, Rolf ^b  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b UNIVERSITY OF MUNICH   (Germany)

Author keywords

Ab initio calculations; Cycloaddition; Density functional calculations; Reaction mechanisms; Thiocarbonyl ylides; Transition states

Indexed keywords

ACTIVATION ENERGY; ADDITION REACTIONS; CHEMICAL BONDS; GROUND STATE; KETONES; STRUCTURE (COMPOSITION);

CYCLOADDITION;

ALDEHYDES;

ACETONE; CARBON; CARBONYL DERIVATIVE; METHYL GROUP; THIOACETONE S METHYLIDE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; CYCLOADDITION; DENSITY; ENERGY; GEOMETRY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0037938780     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200204658     Document Type: Article

References (60)

1. R. Kellogg, Tetrahedron 1976, 32, 2165-2184.
2. R. Huisgen, C. Fulka, I. Kalwinsch, X. Li, G. Mloston, J. R. Moran, A. Pröbstl, Bull. Soc. Chim. Belg. 1984, 993, 511-532.
3. P. K. Klaus, in Methoden der organischen Chemie (Houben-Weyl), Vol. E11/2 (Ed.: D. Klamann), Thieme, Stuttgart, 1985, pp. 1344-1359.
4. G. Mloston, H. Heimgartner, Polish J. Chem. 2000, 74, 1503-1532.
5. G. Mloston, H. Heimgartner, in The Chemistry of Heterocyclic Compounds, Vol. 59 (Eds.: A. Padwa, W. H. Pearson), Wiley, New York, 2002, pp. 315-360.
6. R. Huisgen, I. Kalwinsch, X. Li, G. Mloston, Eur. J. Org. Chem. 2000, 1685-1694.
7. R. Huisgen, X. Li, H. Giera, E. Langhals, Helv. Chim. Acta 2001, 84, 981-999.
8. R. Huisgen, G. Mloston, E. Langhals, Helv. Chim. Acta 2001, 84, 1805-1820.
9. R. Huisgen, G. Mloston, H. Giera, E. Langhals, Tetrahedron 2002, 58, 507-519.
10. R. Huisgen, G. Mloston, E. Langhals, T. Oshima, Helv. Chim. Acta. 2002, 85, 2668-2685.
11. R. Huisgen, Angew. Chem. 1963, 75, 742-754; Angew. Chem. Int. Ed. Engl. 1963, 2, 633; R. Huisgen, J. Org. Chem. 1976, 41, 403-419.
12. R. Huisgen, Angew. Chem. 1963, 75, 742-754; Angew. Chem. Int. Ed. Engl. 1963, 2, 633; R. Huisgen, J. Org. Chem. 1976, 41, 403-419.
13. R. Huisgen, Angew. Chem. 1963, 75, 742-754; Angew. Chem. Int. Ed. Engl. 1963, 2, 633; R. Huisgen, J. Org. Chem. 1976, 41, 403-419.
14. R. Huisgen, in 1,3-Dipolar Cycloaddition Chemistry, Vol. 1 (Ed.: A. Padwa), Wiley Interscience, 1984, pp. 1-176.
15. K. N. Houk, K. Yamaguchi, in 1,3-Dipolar Cycloaddition Chemistry, Vol. 2 (Ed.: A. Padwa), Wiley Interscience, 1984, pp. 407-450.
16. K. N. Houk, Y. Li, J. Storer, L. Raimondi, B. Beno, J. Chem. Soc. Faraday Trans. 1994, 90, 1599-1604.
17. E. Goldstein, B. Beno, K. N. Houk, J. Am. Chem. Soc. 1996, 118, 6036-6043.
18. K. N. Houk, B. R. Beno, M. Nendel, K. Black, H. Y. Yoo, S. Wilsey, J. K. Lee, J. Mol. Struct. (Theochem) 1997, 398-399, 169-179.
19. H. Isobe, Y. Takano, Y. Kitagawa, T. Kawakami, S. Yamanaka, K. Yamaguchi, K. N. Houk, Mol. Physics 2002, 100, 717-727.
20. J. Sauer, R. Sustmann, Angew. Chem. 1980, 92, 773-801; Angew. Chem. Int. Ed. Engl. 1980, 19, 779-807.
21. J. Sauer, R. Sustmann, Angew. Chem. 1980, 92, 773-801; Angew. Chem. Int. Ed. Engl. 1980, 19, 779-807.
22. R. Sustmann, S. Tappanchai, H. Bandmann, J. Am. Chem. Soc. 1996, 118, 12555-12561.
23. R. Sustmann, W. Sicking, J. Am. Chem. Soc. 1996, 118, 12562-12571.
24. E Wurche, F. Klärner, in High Pressure Chemistry, Synthetic, Mechanistic, and Supercritical Applications (Ed.: F.-G. K. R. van Eldik), Wiley-VCH, 2002, pp. 41-96.
25. F.-G. Klärner, F. Wurche, J. Prakt. Chem. 2000, 342, 609-636.
26. F.-G. Klärner, M. K. Diedrich in The Chemistry of Dienes and Polyenes, Vol. 1 (Ed.: Z. Rappoport), Wiley, 1997, pp. 547-617.
27. R. Sustmann, Pure Appl. Chem. 1974, 40, 569-593.
28. J. J. W. McDouall, M. A. Robb, U. Niazi, F. Bernardi, B. Schlegel, J. Am. Chem. Soc. 1987, 109, 4642-4648.
29. R. Sustmann, W. Sicking, R. Huisgen, J. Am. Chem. Soc. 1995, 117, 9679-9685.
30. R. Huisgen, G. Mloston, K. Polborn, R. Sustmann, W. Sicking, Liebigs Ann. Chem. 1997, 179-185.
31. J. Liu, S. Niwayama, Y. You, K. N. Houk, J. Org. Chem. 1998, 63, 1064-1073.
32. Y. Hu, K. N. Houk, Tetrahedron 2000, 56, 8239-8243.
33. A. Rastelli, R. Gandolfi, M. Sarzi-Amadè, J. Org. Chem. 1998, 63, 7425-7436.
34. A. Rastelli, R. Gandolfi, M. Sarzi-Amadè, Adv. Quantum Chem. 2000, 36, 151-167.
35. C. Di Valentin, M. Freccero, R. Gandolfi, A. Rastelli, J. Org. Chem. 2000, 65, 6112-6120.
36. A. Rastelli, R. Gandolfi, M. Sarzi-Amadè, B. Carboni, J. Org. Chem. 2001, 66, 2449-2458.
37. M. Freccero, R. Gandolfi, M. Sarzi-Amadè, A. Rastelli, J. Chem. Soc. Perkin Trans. 2 1998, 2413-2419.
38. M. T. Nguyen, A. K. Chandra, S. Sakai, K. Morokuma, J. Org. Chem. 1999, 64, 65-69.
39. L. R. Domingo, J. Org. Chem. 1999, 64, 3922-3929.
40. F. P. Cossio, T. Morao, H. Jiao, P. v. R. Schleyer, J. Am. Chem. Soc. 1999, 121, 6737-6746.
41. A. Hosomi, Y. Matsuyama, H. Sakurai, J. Chem. Soc. Chem. Commun. 1986, 1073-1074.
42. J. J. P. Stewart, J. Comp. Chem. 1989, 10, 209-220.
43. Gaussian 98 (Revision A.7), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
44. MOLCAS Version 5.4, K. Andersson, M. Barysz, A. Bernhardsson, M. R. A. Blomberg, D. L. Cooper, M. P. Fülscher, C. de Graaf, B. A. Hess, G. Karlstr-m, R. Lindh, P.-A. Malmqvist, T. Nakajima, P. Neogrady, J. Olsen, B. O. Roos, B. Schimmelpfennig, M. Schütz, L. Seijo, L. Serrano-Andres, P. E. M. Siegbahn, J. Stalring, T. Thorsteinsson, V. Veryazov, P.-O. Widmark, Lund University, Sweden, 2002.
45. K. N. Houk, K. Yamaguchi, in 1,3-Dipolar Cycloaddition Chemistry, Vol. 2 (Ed.: A. Padwa), Wiley, New York, 1984, 407-450.
46. E. C. Brown, W. T. Borden, J. Phys. Chem. A 2002, 106, 2963-2969.
47. A. G. Leach, S. Catak, K. N. Houk, Chem. Eur. J. 2002, 8, 1290-1299.
48. J. Fabian, J. Mol. Struct. (Theochem) 1997, 398-399, 411-416.
49. K. Koyano, I. Tanaka, J. Phys. Chem. 1965, 69, 2545-2550.
50. T. S. Dobashi, M. H. Goodrow, E. J. Grubbs, J. Org. Chem. 1973, 38, 4440-4443.
51. H. Hermann, R. Huisgen, H. Mäder, J. Am. Chem. Soc. 1971, 93, 1779-1780.
52. J. E. Fowler, I. L. Alberts, H. F. Schäfer III, J. Am. Chem. Soc. 1991, 113, 4768-4776.
53. E. Vedejs, D. A. Perry, K. N. Houk, N. G. Rondan, J. Am. Chem. Soc. 1983, 105, 6999-7001.
54. D. P. Stevenson, J. Y. Beach, J. Am. Chem. Soc. 1938, 60, 2872-2876.
55. L. B. Brahde, Acta Chem. Scand. 1954, 8, 1145-1151.
56. Z. Nahlovski, B. Nahlovska, H. M. Seip, Acta Chem. Scand. 1969, 23, 3534-3540.
57. L. Fiscra, R. Huisgen, I. Kalwinsch, E. Langhals, X. Li, G. Mloston, K. Polborn, W. Sicking, R. Sustmann, Pure Appl. Chem. 1996, 68, 789-798.
58. R. Huisgen, G. Mloston, K. Polborn, R. Sustmann, Chem. Eur. J. 2003, 9, 2256-2263.
59. K. N. Houk, J. Gonzalez, Y. Li, Acc. Chem. Res. 1995, 28, 81-90.
60. R. Huisgen, in 1,3-Dipolar Cycloaddition Chemistry, Vol. 1 (Ed.: A. Padwa), Wiley, New York, 1984, 1-176.