Recent advances in stereodynamics and conformational analysis by dynamic NMR and theoretical calculations

European Journal of Organic Chemistry

Volumn , Issue 11, 2010, Pages 2035-2056

  Casarini, Daniele ^a   Lunazzi, Lodovico ^b   Mazzanti, Andrea ^b  

^a UNIVERSITY OF BASILICATA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Atropisomerism; Conformation analysis; Density functional calculations; Molecular motions; NMR spectroscopy

Indexed keywords

EID: 77950210569     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901340     Document Type: Short Survey

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174. A two-letter designation has been used to name conformations. The first letter defines the orientation of the propargyl quaternary carbon (G denotes gauche to the lone pair and to the N-methyl group; G′ denotes gauche to the lone pair and to the isopropyl group; A denotes anti to the lone pair). The second letter defines the orientation of the isopropyl methine proton (G denotes gauche to the lone pair and to the N-methyl group; G′ denotes gauche to the lone pair and to the propargyl group; A denotes anti to the lone pair).
175. J. G. Jewett, J. J. Breeyear, J. H. Brown, C. H. Bushweller, J. Am. Chem. Soc. 2000, 122, 308-323.
176. For a similar compound see: J. E. Anderson, D. Casarini, A. I. Ijeh, L. Lunazzi, D. A. Tocher, J. Am. Chem. Soc. 1995, 117, 3054-3056.
177. Other cases in which a barrier cannot be observed until the lower barrier is frozen have been reported: a) W. R. Jackson, W. B. Jennings, Tetrahedron Lett. 1974, 15, 1837-1838;
178. b) J. E. Anderson, D. Casarini, A. J. Ijeh, L. Lunazzi, J. Am. Chem. Soc. 1997, 119, 8050-8057;
179. c) D. Casarini, L. Lunazzi, A. Mazzanti, E. Foresti, J. Org. Chem. 1998, 63, 4746-4754;
180. d) L. Lunazzi, A. Mazzanti, A. Muñoz Álvarez, J. Org. Chem. 2000, 65, 3200-3206.
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183. 2, as in: L. T. Scott, M. M. Hashemi, M. S. Bratcher, J. Am. Chem. Soc. 1992, 114, 1920-1921.
184. Y. Wang, A. D. Stretton, M. C. McConnell, P. A. Wood, S. Parsons, J. B. Henry, A. R. Mount, T. H. Galow, J. Am. Chem. Soc. 2007, 129, 13193-13200.
185. G. Schwab, D. Stern, D. Stalke, J. Org. Chem. 2008, 73, 5242-5247.
186. G. Bartoli, S. Grilli, L. Lunazzi, M. Massaccesi, A. Mazzanti, S. Rinaldi, J. Org. Chem. 2002, 67, 2659-2664.
187. B. A. Shainyan, V. I. Meshcheryakov, A. I. Albanov, M. V. Sigalov, Tetrahedron Lett. 2005, 46, 6199-6201.
188. B. A. Shainyan, I. A. Ushakov, A. Koch, E. Kleinpeter, J. Org. Chem. 2006, 71, 7638-7642.
189. B. A. Shainyan, I. A. Ushakov, V. I. Meshcheryakov, U. Schilde, A. Koch, E. Kleinpeter, Tetrahedron 2007, 63, 11828-11837.
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