The Journal of Organic Chemistry
Article
CDCl3, δ ppm): 173.8, 60.0, 34.3, 31.8, 29.5, 29.4, 29.28, 29.24, 29.1,
24.9, 22.6, 14.2, 14.0.
(7) Fuentes, J. A.; Slawin, A. M. Z.; Clarke, M. L. Catal. Sci. Technol.
2012, 2, 715 and reference therein.
Propyl Undecanoate (2ac). Light yellow oil, 173.4 mg, 78% yield,
L/B = 85:15. 1H NMR (400 MHz, CDCl3, δ ppm): 4.00 (t, J = 6.7 Hz,
2H), 2.26 (t, J = 7.5 Hz, 2H), 1.77−1.43 (m, 4H), 1.32−1.18 (m, 14
H), 0.91 (t, J = 7.4 Hz, 3H), 0.83 (t, J = 6.8 Hz, 3H). 13C{1H}-NMR
(400 MHz, CDCl3, δ ppm): 173.9, 65.7, 34.3, 31.8, 29.5, 29.4, 29.29,
29.26, 29.1, 25.0, 22.6, 22.0, 14.0, 10.3.
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Commun. 2001, 1, 1476. (c) Furst, M. R. L.; Goff, R. L.; Quinzler, D.;
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Cole-Hamilton, D. J. Chem. Commun. 2004, 1720.
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́
(b) Yang, Q.; Cao, H.; Robertson, A.; Alper, H. J. Org. Chem. 2010, 75,
6297.
Isopropyl Undecanoate (3ac). Yellow oil, 198.5 mg, 89% yield,
1
L/B = 90:10. H NMR (400 MHz, CDCl3, δ ppm): 4.97 (m, 1H),
2.22 (t, J = 7.5 Hz, 2H), 1.59−1.54 (m, 2H), 1.33−1.10 (m, 20H),
6.84 (t, J = 6.8 Hz, 3H). 13C{1H}-NMR (400 MHz, CDCl3, δ ppm):
173.4, 67.7, 34.7, 31.8, 29.5, 29.4, 29.29, 29.26, 29.1, 25.0, 22.6, 21.8,
14.0.
(10) Kawashima, K.; Okano, K.; Nozaki, K.; Hiyama, T. Bull. Chem.
Soc. Jpn. 2004, 77, 347.
(11) Fuentes, J. A.; S, A. M. Z.; Clarke, M. L. Catal. Sci. Technol.
2012, 2, 715.
Phenyl Undecanoate (4ac). Light yellow oil, 149.4 mg, 68%
yield, L/B = 80:20. 1H NMR (400 MHz, CDCl3, δ ppm): 7.36 (t, J =
8.0 Hz, 2H), 7.20 (t, J = 7.4 Hz, 1H), 7.06 (dd, J = 8.5 Hz, 1.0 Hz, 2
H), 2.54 (t, J = 7.5 Hz, 2H), 1.78−1.70 (m, 2H), 1.32−1.17 (m, 14H),
0.87 (t, J = 6.8 Hz, 3H). 13C{1H}-NMR (400 MHz, CDCl3, δ ppm):
172.3, 150.8, 129.3, 125.7, 121.5, 34.4, 31.9, 29.5, 29.4, 29.3, 29.2, 29.1,
24.9, 22.6, 14.1.
(12) Fuchikami, T.; Ohishi, K.; Ojima, I.; February, R. J. Org. Chem.
1983, 48, 3803.
(13) Jain, P. S.; Todarwal, A. A.; Bari, S. B.; Surana, S. J. Pharmacog.
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(14) Zimmermann, F.; Meux, E.; Mieloszynski, J.-L.; Lecuire, J.-M.;
Oget, N. Tetrahedron Lett. 2005, 46, 3201.
(15) Dutta, A.; Patra, A. K.; Uyama, H.; Bhaumik, A. ACS Appl.
Mater. Interfaces 2013, 5, 9913.
ASSOCIATED CONTENT
(16) Ryu, I.; Uehara, S.; Hirao, H.; Fukuyama, T. Org. Lett. 2008, 10,
1005.
(17) Deshmukh, A. R.; Tran, L.; Biehl, E. R. J. Org. Chem. 1992, 57,
667.
(18) Miyamoto, K.; Sei, Y.; Yamaguchi, K.; Ochiai, M. J. Am. Chem.
Soc. 2009, 131, 1382.
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S
* Supporting Information
1H and 13C spectra and spectral data. The Supporting
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We are grateful to Cytec Canada Inc. and to the Natural
Sciences and Engineering Research Council of Canada
(NSERC) for financial support. We are also indebted to
Cytec Canada Inc. for the generous supply of the
phosphaadamantane ligand CYTOP 292.
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