Allenyl azide cycloaddition chemistry: Exploration of the scope and mechanism of cyclopentennelated dihydropyrrole synthesis through azatrimethylenemethane intermediates

Journal of Organic Chemistry

Volumn 73, Issue 13, 2008, Pages 5090-5099

  Feldman, Ken S ^a   Iyer, Malliga R ^a   López, Carlos Silva ^b   Faza, Olalla Nieto ^b  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF VIGO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CALCULATIONS; CHEMICAL REACTIONS; ORGANIC COMPOUNDS;

ALLENYL; AMERICAN CHEMICAL SOCIETY (ACS); CHEMICAL EQUATIONS; CYCLOADDITION CHEMISTRY; DENSITY FUNCTIONAL CALCULATIONS; DIASTEREO SELECTIVITY; DIHYDROPYRROLE; ELECTROCYCLIZATION; PLANARITY; SYNTHESIS (OF CHIRAL IONIC LIQUIDS); WOODWARD (CO);

PROBABILITY DENSITY FUNCTION;

ALLENE DERIVATIVE; AZATRIMETHYLENEMETHANE; AZIDE; FURAN DERIVATIVE; METHANE; PYRROLE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; ELECTROSPRAY MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AZA COMPOUNDS; AZIDES; COMBINATORIAL CHEMISTRY TECHNIQUES; COMPUTER SIMULATION; METHANE; MOLECULAR STRUCTURE; PYRROLES;

EID: 46849106323     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8008066     Document Type: Article

References (43)

1. Feldman, K. S.; Iyer, M. R. J. Am. Chem. Soc. 2005, 127, 4590-4591.
2. (a) López, C. S.; Faza, O. N.; Feldman, K. S.; Iyer, M. R.; Hester, D. K, II J. Am. Chem. Soc. 2007, 129, 7638-7646.
3. (b) The reaction profile of the related oxatrimethylenemethane species has been explored via density functional and CASSCF methods; see ref 19a.
4. (a) Tsang, W.; Hampson, R. F. J. Phys. Chem. Ref. Data 1986, 15, 1087-1222. (see pg. 1095).
5. (b) Parkes, D. A.; Quinn, C. P J. Chem. Soc. Farad. Soc. 1 1976, 72, 1952-1970.
6. (c) Tsang, W. J. Am. Chem. Soc. 1985, 107, 2872-2880.
7. (d) Choo, K. Y.; Beadle, P. C.; Piszkiewicz, W.; Golden, D. M. Int. J. Chem. Kinet. 1976, 8, 45-58.
8. (a) Quast, H.; Meichsner, G. Chem. Ber. 1987, 120, 1049-1058.
9. (b) Quast, H.; Fuß, A.; Heublein, A.; Jakobi, H.; Seiferling, B. Chem. Ber. 1991, 124, 2545-2554.
10. Bleiholder, R. F.; Shechter, H. J. Am. Chem. Soc. 1968, 90, 2131-2137.
11. Bingham, E. M.; Gilbert, J. C. J. Org. Chem. 1975, 40, 224-228.
12. Barraclough, D.; Moorhouse, N. P.; Onwuyali, E. I.; Scheinmann, F.; Hursthouse, M. B.; Galas, A. M. R. J. Chem. Res., Synop. 1984, 10, 2-103.
13. Mukai, C.; Kobayashi, M.; Kubota, S.; Takahashi, Y.; Kitagaki, S. J. Org. Chem. 2004, 69, 2128-2136.
14. (a) Rule, M.; Salinaro, R. F.; Pratt, D. R.; Berson, J. A. J. Am. Chem. Soc. 1982, 104, 2223-2228.
15. (b) Feldman, K. S.; Mareska, D. A. J. Org. Chem. 1999, 64, 5650-5660.
16. Boyer, J. H. J. Am. Chem. Soc. 1951, 73, 5248-5252.
17. (a) Jansen, A.; Krause, N. Synthesis 2002, 1987-1992.
18. (b) Konno, T.; Tanikawa, M.; Ishihara, T.; Yamanaka, H. Collect. Czech. Chem. Commun. 2002, 67, 1421-1435.
19. (a) Bernauer, K.; Englert, G.; Vetter, W.; Weis, E. Helv. Chim. Acta 1969, 52, 1886-1905.
20. Synthesis studies: (b) Lévy, J.; Hugel, G. J. Org. Chem. 1986, 51, 1594-1595.
21. (c) Overman, L. E.; Robertson, G. M.; Robichaud, A. J. J. Am. Chem. Soc. 1991, 113, 2598-2610.
22. (d) Schultz, A. G.; Dai, M. Tetrahedron Lett. 1999, 40, 645-648.
23. (a) Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864-B871.
24. (b) Kohn, W.; Sham, L. Phys. Rev. A 1965, 140, A1133-A1138.
25. (c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11637.
26. (d) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
27. (e) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
28. Brinker, U. H.; König, L. Chem. Ber. 1983, 116, 882-893.
29. Cichra, D. A.; Duncan, C. D.; Berson, J. A. J. Am. Chem. Soc. 1980, 102, 6527-6533.
30. (a) Roth, W. R.; Schmidt, T. Tetrahedron Lett. 1971, 3639-3642.
31. (b) Kende, A. S.; Riecke, E. E. J. Am. Chem. Soc. 1972, 94, 1397-1399.
32. (c) Gilbert, J. C.; Higley, D. P. Tetrahedron Lett. 1973, 2075-2078.
33. (d) Davidson, E. R.; Gajewski, J. J.; Shook, C. A.; Cohen, T. J. Am. Chem. Soc. 1995, 117, 8495-8501.
34. (e) Maier, G.; Senger, S. J. Am. Chem. Soc. 1997, 119, 5857-5861.
35. Frisch, M. J. Gaussian03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
36. Bauernschmitt, R.; Ahlrichs, R. J. Chem. Phys. 1996, 22, 9047-9052.
37. (a) Hess, B. A., Jr.; Eckart, U.; Fabian, J. J. Am. Chem. Soc. 1998, 120, 12310-12315.
38. (b) Hess, B.A., Jr.; Smentek, L.; Brash, A. R.; Cha, J. K. J. Am. Chem. Soc. 1999, 121, 5603-5604.
39. (c) López, C. S.; Faza, O. N.; York, D. M.; de Lera, A. J. Org. Chem. 2004, 69, 3635-3644.
40. (d) Li, J.; Worthington, S. E.; Cramer, C. J. J. Chem. Soc., Perkin Trans. 2 1998, 1045-1052.
41. Knochel, P.; Rao, C. J. Tetrahedron 1993, 49, 29-48.
42. Muratake, H.; Natsume, M.; Nakai, H. Tetrahedron 2004, 60, 11783-11803.
43. Marino, J. P.; McClure, M. S.; Holub, D. P.; Comasseto, J. V.; Tucci, F. C. J. Am. Chem. Soc. 2002, 124, 1664-1668.