Communication
RSC Advances
10 L. Liu and P. E. Floreancig, Org. Lett., 2010, 12, 4686–
4689.
Experimental section
11 L.-Q. Cui, Z.-L. Dong, K. Liu and C. Zhang, Org. Lett., 2011,
13, 6488–6491.
12 X. Zhang, L. Xu, X. Wang, N. Ma and F. Sun, Chin. J. Chem.,
2012, 30, 1525–1530.
13 P. P. Fu and R. G. Harvey, Tetrahedron Lett., 1974, 15, 3217–
3220.
14 Y. Xu and L. Lin, Appl. Catal., A, 1999, 188, 53–67.
15 J. M. Neely and T. Rovis, J. Am. Chem. Soc., 2012, 135, 66–69.
16 J. L. Costa, A. F. Noels, A. J. Hubert and P. Teyssie,
Tetrahedron Lett., 1984, 25, 649–650.
Typical procedure for dehydrogenation of cyclohexene-carbox-
ylic acids: 3,4-dimethylcyclohex-3-enecarboxylic acid (1d,
308 mg, 0.2 mmol) and H2SO4 (98 wt%, 3 mL) were added to a
ask with a magnetic stirring bar. The reaction mixture was
stirred at 100 ꢀC for 15 min and then poured into excess ice
water (5 mL) with stirring. The precipitated raw product was
collected by ltration and washed with cool water for three
times. The resultant product 2c was white solid (249 mg,
0.166 mmol, and yield: 83%).
17 T. A. Ramirez, B. Zhao and Y. Shi, Tetrahedron Lett., 2010, 51,
1822–1825.
Acknowledgements
18 (a) R. Yamaguchi, C. Ikeda, Y. Takahashi and K.-i. Fujita,
J. Am. Chem. Soc., 2009, 131, 8410–8412; (b) A. M. Royer,
T. B. Rauchfuss and D. L. Gray, Organometallics, 2010, 29,
6763–6768; (c) A. Thawani, R. Rajeev and R. B. Sunoj,
Chem. – Eur. J., 2013, 19, 4069–4077.
This work was supported by Biomass Research and Develop-
ment Initiative Competitive Grant no. 2001-10006-3058 from
the USDA National Institute of Food and Agriculture and the
start-up funding from IFAS at the University of Florid to Z. T.
´
19 (a) M. F. Williams, B. Fonfe, A. Jentys, C. Breitkopf,
Notes and references
J. A. R. van Veen and J. A. Lercher, J. Phys. Chem. C, 2010,
114, 14532–14541; (b) W. Ninomiya, Y. Tanabe,
K.-I. Sotowa, T. Yasukawa and S. Sugiyama, Res. Chem.
Intermed., 2008, 34, 663–668.
1 (a) J. J. Bozell and G. R. Petersen, Green Chem., 2010, 12, 539–
554; (b) G.-Q. Chen and M. K. Patel, Chem. Rev., 2011, 112,
2082–2099; (c) P. N. R. Vennestrøm, C. M. Osmundsen,
C. H. Christensen and E. Taarning, Angew. Chem., Int. Ed.,
2011, 50, 10502–10509; (d) D. R. Dodds and R. A. Gross,
Science, 2007, 318, 1250–1251.
2 J. M. Beale and J. Block, Organic medicinal and pharmaceutical
chemistry, Lippincott Williams & Wilkins, 2010.
3 M. P. Stevens, Polymer chemistry, Oxford University Press,
New York, 1990, vol. 2.
4 (a) P. P. Fu and R. G. Harvey, Chem. Rev., 1978, 78, 317–361; (b)
J. Choi, A. H. R. MacArthur, M. Brookhart and A. S. Goldman,
Chem. Rev., 2011, 111, 1761–1779; (c) G. E. Dobereiner and
R. H. Crabtree, Chem. Rev., 2009, 110, 681–703.
5 (a) G. N. Varseev and M. E. Maier, Org. Lett., 2005, 7, 3881–
3884; (b) H. S. Taylor and H. Fehrer, J. Am. Chem. Soc.,
1941, 63, 1387–1392; (c) H. Zheng, D. Ma, X. Bao, J. Z. Hu,
J. H. Kwak, Y. Wang and C. H. F. Peden, J. Am. Chem. Soc.,
2008, 130, 3722–3723.
20 C. S. Yi and D. W. Lee, Organometallics, 2009, 28, 947–949.
21 (a) T. Diao and S. S. Stahl, J. Am. Chem. Soc., 2011, 133,
14566–14569; (b) S. R. Kandukuri and M. Oestreich, J. Org.
Chem., 2012, 77, 8750–8755; (c) T. Ohmura, A. Kijima and
M. Suginome, Org. Lett., 2011, 13, 1238–1241; (d)
S. S. Stahl, Science, 2005, 309, 1824–1826; (e) J. Cossy and
D. Belotti, Org. Lett., 2002, 4, 2557–2559; (f) T. Tanaka,
K.-i. Okunaga and M. Hayashi, Tetrahedron Lett., 2010, 51,
4633–4635.
22 K. Alder and H. A. Dortmann, Chem. Ber., 1952, 85, 556–565.
23 D. L. Sikkenga, A. K. Pandya, I. C. Zaenger, K. J. Abrams and
T. M. Bartos, US Pat., 6 562 997, 2003.
24 B. Kuczenski and R. Geyer, Resour., Conserv. Recycl., 2010, 54,
1161–1169.
25 R. R. Fall, J. Kuzma and M. Nemecek-Marshall, US pat., 5 849
970 B2, 1998.
26 (a) Y. Doleyres, P. Beck, S. Vollenweider and C. Lacroix, Appl.
Microbiol. Biotechnol., 2005, 68, 467–474; (b) S. Vollenweider
and C. Lacroix, Appl. Microbiol. Biotechnol., 2004, 64, 16–27.
27 (a) K. Furuta, Y. Miwa, K. Iwanaga and H. Yamamoto, J. Am.
Chem. Soc., 1988, 110, 6254–6255; (b) G. Cahiez, J. Rivas-
Enterrios and P. Clery, Tetrahedron Lett., 1988, 29, 3659–
3662.
6 E. C. Horning, J. Am. Chem. Soc., 1945, 67, 1421–1422.
7 H. A. Silverwood and M. Orchin, J. Org. Chem., 1962, 27,
3401–3404.
8 J. G. Lee and K. C. Kim, Tetrahedron Lett., 1992, 33, 6363–
6366.
´
´
´
9 M. Filipan-Litvic, M. Litvic and V. Vinkovic, Tetrahedron,
2008, 64, 5649–5656.
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