Bond rotation dynamics of N-cycloalkenyl-N-benzyl α-haloacetamide derivatives

Journal of Organic Chemistry

Volumn 74, Issue 11, 2009, Pages 4262-4266

  Guthrie, David B ^a   Damodaran, Krishnan ^a   Curran, Dennis P ^a   Wilson, Paul ^b   Clark, Andrew J ^b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL; AMBIENT TEMPERATURES; BOND ROTATIONS; CHEMICAL EQUATIONS; DIASTEREOMERS; RADICAL CYCLIZATIONS; RING SIZES; VARIABLE-TEMPERATURE NMR;

AMIDES; CHEMICAL REACTIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ROTATION;

AMIDE; CYCLOALKENE; FUNCTIONAL GROUP; N CYCLOALKENYL N BENZYL ALPHA HALOACETAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE;

ACETAMIDES; ALKENES; CYCLIZATION; KINETICS; MOLECULAR CONFORMATION; THERMODYNAMICS;

EID: 66249110301     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900491w     Document Type: Article

References (25)

1. (a) Ishibashi, H.; Sato, T.; Ikeda, M. Synthesis 2002, 695-713.
2. (b) Alabugin, I. V.; Manoharan, M. J. Am. Chem. Soc. 2005, 127, 9534-9545.
3. (a) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545.
4. (b) Ishibashi, H.; Ishita, A.; Tamura, O. Tetrahedron Lett. 2002, 43, 473-475.
5. (a) Clark, A. J.; Dell, C. P.; Ellard, J. M.; Hunt, N. A.; McDonagh, J. P. Tetrahedron Lett. 1999, 40, 8619-8623.
6. (b) Clark, A. J.; Dell, C. P.; McDonagh, J. P. C. R. Acad. Sci. Ser. II C 2001, 4, 575-579.
7. (c) Clark, A. J.; Dell, C. P.; McDonagh, J. M.; Geden, J.; Mawdsley, P. Org. Lett. 2003, 5, 2063-2066.
8. Chatgilialoglu, C.; Ferreri, C.; Guerra, M.; Timokhin, V.; Froudakis, G.; Gimisis, T. J. Am. Chem. Soc. 2002, 124, 10765-10772.
9. Curran, D. P.; Guthrie, D. B.; Geib, S. J. J. Am. Chem. Soc. 2008, 130, 8437-8445.
10. Taniguchi, T.; Yonei, D.; Sasaki, M.; Tamura, O.; Ishibashi, H. Tetrahedron 2008, 64, 2634-2641.
11. (a) Stork, G.; Mah, R. Heterocycles 1989, 28, 723-727.
12. (b) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750.
13. (c) Musa, O. M.; Choi, S. Y.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1998, 63, 786-793.
14. (d) Musa, O. M.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1999, 64, 1022-1025.
15. Ahlbrecht, H.; Becher, G.; Blecher, J.; Kalinowski, H. O.; Raab, W.; Mannschreck, A. Tetrahedron Lett. 1979, 20, 2265-2268.
16. Wolf, C. Dynamic Stereochemistry of Organic Compounds; RSC Publishing: Cambridge, UK, 2008; pp 94-104; see especially "non-biaryl atropisomers".
17. (a) Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131-3132.
18. (b) Curran, D. P.; Hale, G. R.; Geib, S. J.; Balog, A.; Cass, Q. B.; Degani, A. L. G.; Hernandes, M. Z.; Freitas, L. C. G. Tetrahedron: Asymmetry 1997, 8, 3955-3975.
19. (a) Curran, D. P.; Chen, C. H. T.; Geib, S. J.; Lapierre, A. J. B. Tetrahedron 2004, 60, 4413-4424.
20. (b) Petit, M.; Geib, S. J.; Curran, D. P. Tetrahedron 2004, 60, 7543-7552.
21. (c) Lapierre, A. J. B.; Geib, S. J.; Curran, D. P. J. Am. Chem. Soc. 2007, 129, 494-495.
22. Reich, H. J. J. Chem. Educ. Software 1996, 3D2.
23. Yamada, S. Rev. Heteroatom. Chem. 1999, 19, 203-236.
24. Musa, O. M.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1999, 64, 1022-1025.
25. 2 alkenyl group is a model for a radical.