On the interactions of N,N′-bismesitylimidazolin-2-yl and alcohols

Tetrahedron Letters

Volumn 49, Issue 27, 2008, Pages 4316-4318

  Schmidt, Michael A ^a   Müller, Peter ^a   Movassaghi, Mohammad ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBENOID; HETEROCYCLIC COMPOUND; IMIDAZOLINE DERIVATIVE; N,N' BISMESITYLIMIDAZOLIN 2 YL; NITROGEN HETEROCYCLIC CARBENE DERIVATIVE; VOLATILE AGENT;

AMIDATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 44249108530     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.091     Document Type: Article

References (21)

1. Arduengo III A.J., Dias H.V.R., Harlow R.L., and Kline M. J. Am. Chem. Soc. 114 (1992) 5530
2. Arduengo III A.J., Harlow R.L., and Kline M. J. Am. Chem. Soc. 113 (1991) 361
3. Wanzlick H.-W., and Kleiner H.-J. Angew. Chem. 73 (1961) 493
4. Wanzlick H.-W., and Schikora E. Angew. Chem. 71 (1960) 494
5. For representative examples, see:. Herrmann W.A. Angew. Chem., Int. Ed. 41 (2002) 1290
6. Bourissou D., Guerret O., Gabbai F.P., and Bertrand G. Chem. Rev. 100 (2000) 39
7. Cowley A.H. J. Organomet. Chem. 617-618 (2001) 105
8. For a review, see:. Clavier H., and Nolan S.P. Annu. Rep. Prog. Chem., Sect. B 103 (2007) 193
9. For an extensive review, see:. Enders D., Niemeier O., and Henseler A. Chem. Rev. 107 (2007) 5606
10. Movasssaghi M., and Schmidt M.A. Org. Lett. 7 (2005) 2453
11. 2 on all data by full-matrix least squares with shelxl-97 [Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112]. All non-hydrogen atoms, were refined anisotropically. All hydrogen atoms bonded to carbon atoms (except the hydrogen on carbon C(2′) in the structure of 4) were included into the model at geometrically calculated positions and refined using a riding model. Coordinates for the other hydrogen atoms were taken from the difference Fourier synthesis and refined semi-freely with the help of a distance restraint. The isotropic displacement parameters of all hydrogen atoms were constrained to 1.2 times the U value of the atoms they are linked to (1.5 times for methyl groups).
12. Arduengo III A.J., Gamper S.F., Tamm M., Calabrese J.C., Davidson F., and Craig H.A. J. Am. Chem. Soc. 117 (1995) 572
13. For a related important structure, see:. Cowan J.A., Clyburne J.A.C., Davidson M.G., Harris R.L.W., Howard J.A.K., Küpper P., Leech M.A., and Richards S.P. Angew. Chem., Int. Ed. 41 (2002) 1432
14. The pKa of TFE in DMSO is 23.5 while that of methanol is 29.0. Olmstead W.N., Margolin Z., and Bordwell F.G. J. Org. Chem. 45 (1980) 3295
15. 8 in an effort to look for two distinct sets of resonances; however, precipitation resulted during sample cooling due to diminished solubility of the solutes.
16. The proton originating from TFE shifts up-field from 10.75 ppm at 20 °C to 9.85 ppm at 70 °C. Imidazolium cations with coordination anions such as chloride have C2 resonances at 11.1 ppm, while those with non-coordinating anions such as tetrafluoroborate resonate at 8.6 ppm; see:. Grasa G.A., Singh R., Scott N.M., Stevens E.D., and Nolan S.P. Chem. Commun. (2004) 2890
17. Denk M.K., and Rodezno J.M. J. Organomet. Chem. 617-618 (2001) 737
18. CD = 34.0 Hz). The signal broadening and the absence of carbon-deuterium spin coupling suggest rapid equilibrium/D-exchange.
19. Addition of water increases in the intensity of the residual protium resonance corresponding to C4/5 and ROH.
20. Yamaguchi Y., Kashiwabara T., Ogata K., Miura Y., Nakamura Y., Kobayashi K., and Ito T. Chem. Commun. 19 (2004) 2160
21. Wang H.M.J., and Lin I.J.B. Organometallics 17 (1998) 972