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B. Barhate, A. S. Gajare, R. D. Wakharkar and A. V. Bedekar, Tetrahe-
dron Lett., 1998, 39, 6349; (c) N. B. Barhate, A. S. Gajare, R.
D. Wakharkar and A. V. Bedekar, Tetrahedron, 1999, 55, 11127;
(d) U. Bora, G. Bose, M. K. Chaudhuri, S. S. Dhar, R. Gopinath, A.
T. Khan and B. K. Patel, Org. Lett., 2000, 2, 247.
trans-2,3-Dibromo-3-(3,4-dichlorophenyl)-1-(pyridin-2-yl)
propan-1-one 6k. IR (KBr) cm−1 3014, 1704, 1581, 1474,
1437, 1409, 1356, 1308, 1288, 1247, 1218, 1152, 1133, 1033,
995, 984, 918, 819, 744, 681, 617, 593; 1H NMR (CDCl3,
300 MHz) δ 8.78 (dd, J = 4.7, 0.6 Hz, 1H), 8.23 (d, J = 7.8 Hz,
1H), 7.94 (td, J = 7.7, 1.6 Hz, 1H), 7.67 (d, J = 2.1 Hz, 1H),
7.59 (ddd, J = 7.5, 4.7, 1.1 Hz, 1H), 7.51 (d, J = 8.3 Hz, 1H),
7.41 (dd, J = 8.3, 2.1 Hz, 1H), 6.67 (d, J = 11.8 Hz, 1H),
5.58 (d, J = 11.8 Hz, 1H); 13C NMR (CDCl3, 75 MHz) δ
191.6, 150.6, 149.4, 138.9, 137.6, 133.5, 133.1, 131.0,
130.5, 128.3, 127.9, 123.8, 47.6, 45.0; HRMS [M+–Br]
calcd for C14H9NO35Cl279Br: m/z 355.9245, found m/z
355.9237.
6 (a) R. K. Dieter, L. E. Nice and S. E. Velu, Tetrahedron Lett., 1996, 37,
2377; (b) K.-M. Kim and I.-H. Park, Synthesis, 2004, 2641.
7 (a) V. Nair, S. B. Panicker, A. Augustine, T. G. George, S. Thomas and
M. Vairamani, Tetrahedron, 2001, 57, 7417; (b) S. C. Roy, C. Guin, K.
K. Rana and G. Maiti, Tetrahedron Lett., 2001, 42, 6941.
trans-2,3-Dibromo-1-(pyridin-2-yl)-3-p-tolylpropan-1-one 6l.
IR (KBr) cm−1 3017, 1706, 1612, 1581, 1513, 1435, 1362,
1319, 1301, 1250, 1219, 1146, 995, 981, 814, 753, 742, 722,
8 C. Ye and J. M. Shreeve, J. Org. Chem., 2004, 69, 8561.
9 A. Subbarayappa, S. Ghosh, P. U. Patoliya, G. Ramachandraiah,
M. Agrawal, M. R. Gandhi, S. C. Upadhyay, P. K. Ghosh and B.
C. Ranu, Green Chem., 2008, 10, 232.
1
671, 617, 577; H NMR (CDCl3, 300 MHz) δ 8.79 (dd, J = 4.7,
10 For reviews, see: (a) G.-W. Wang, Fullerene mechanochemistry. in Ency-
clopedia of Nanoscience and Nanotechnology, ed. H. S. Nalwa, American
Scientific Publishers, Stevenson Ranch, 2004, vol. 3, p. 557;
(b) K. Komatsu, Top. Curr. Chem., 2005, 254, 185; (c) B. Rodríguez,
A. Bruckmann, T. Rantanen and C. Bolm, Adv. Synth. Catal., 2007, 349,
2213; (d) A. L. Garay, A. Pichon and S. L. James, Chem. Soc. Rev.,
2007, 36, 846; (e) A. Bruckmann, A. Krebs and C. Bolm, Green Chem.,
2008, 10, 1131; (f) G. Kaupp, CrystEngComm, 2009, 11, 388;
(g) A. Stolle, T. Szuppa, S. E. S. Leonhardt and B. Ondruschka, Chem.
Soc. Rev., 2011, 40, 2317.
11 For reactions of fullerenes under ball-milling conditions, see: (a) G.-
W. Wang, Y. Murata, K. Komatsu and T. S. M. Wan, Chem. Commun.,
1996, 2059; (b) G.-W. Wang, K. Komatsu, Y. Murata and M. Shiro,
Nature, 1997, 387, 583; (c) K. Komatsu, G.-W. Wang, Y. Murata,
T. Tanaka, K. Fujiwara, K. Yamamoto and M. Saunders, J. Org. Chem.,
1998, 63, 9358; (d) G.-W. Wang, T.-H. Zhang, E.-H. Hao, L.-J. Jiao,
Y. Murata and K. Komatsu, Tetrahedron, 2003, 59, 55; (e) G.-W. Wang,
T.-H. Zhang, Y.-J. Li, P. Lu, H. Zhan, Y.-C. Liu, Y. Murata and
K. Komatsu, Tetrahedron Lett., 2003, 44, 4407; (f) G.-W. Wang, Y.-J. Li,
R.-F. Peng, Z.-H. Liang and Y.-C. Liu, Tetrahedron, 2004, 60, 3921;
(g) R.-F. Peng, G.-W. Wang, Y.-B. Shen, Y.-J. Li, T.-H. Zhang, Y.-C. Liu,
Y. Murata and K. Komatsu, Synth. Commun., 2004, 34, 2117; (h) T.-
H. Zhang, G.-W. Wang, P. Lu, Y.-J. Li, R.-F. Peng, Y.-C. Liu, Y. Murata
and K. Komatsu, Org. Biomol. Chem., 2004, 2, 1698; (i) Y.-J. Li, R.-
F. Peng, Y.-C. Liu and G.-W. Wang, Chin. Chem. Lett., 2004, 15, 1265;
( j) X. Cheng, G.-W. Wang, Y. Murata and K. Komatsu, Chin. Chem.
Lett., 2005, 16, 1327; (k) G.-W. Wang, Z.-X. Chen, Y. Murata and
K. Komatsu, Tetrahedron, 2005, 61, 4851.
0.6 Hz, 1H), 8.24 (d, J = 7.8 Hz, 1H), 7.93 (td, J = 7.7, 1.7 Hz,
1H), 7.58 (ddd, J = 7.6, 4.7, 1.0 Hz, 1H), 7.47 (d, J = 8.1 Hz,
2H), 7.24 (d, J = 8.1 Hz, 2H), 6.79 (d, J = 11.9 Hz, 1H), 5.67
(d, J = 11.9 Hz, 1H), 2.39 (s, 3H); 13C NMR (CDCl3, 75 MHz)
δ 192.2, 150.9, 149.4, 139.4, 137.4, 135.6, 129.7, 128.4, 128.1,
123.7, 50.0, 45.5, 21.4; HRMS [M+–Br] calcd for
C15H13NO79Br: m/z 302.0181, found m/z 302.0175.
trans-3,4-Dibromo-4-phenylbutan-2-one 6m.4h,6b,8 1H NMR
(CDCl3, 300 MHz) δ 7.43–7.36 (m, 5 H), 5.32 (d, J = 11.7 Hz,
1H), 4.93 (d, J = 11.7 Hz, 1H), 2.49 (s, 3H).
trans-Methyl 2,3-dibromo-3-phenylpropanoate 6n.5c,8 1H
NMR (CDCl3, 300 MHz) δ 7.41–7.37 (m, 5H), 5.34 (d, J = 11.7
Hz, 1H), 4.84 (d, J = 11.7 Hz, 1H), 3.90 (s, 3H).
1-(1,2-Dibromoethyl)benzene
9.26 1H
NMR
(CDCl3,
300 MHz) δ 7.41–7.32 (m, 5H), 5.15 (dd, J = 10.4, 5.7 Hz, 1H),
4.08 (dd, J = 10.4, 5.7 Hz, 1H), 4.02 (t, J = 10.4 Hz, 1H).
trans-3,6-Dibromocyclohexene 10.17b 1H NMR (CDCl3,
300 MHz) δ 6.00 (bs, 2H), 4.90 (bs, 2H), 2.47 (d, J = 10.8 Hz,
2H), 2.17 (d, J = 10.8 Hz, 2H).
12 For reactions of non-fullerene molecules under ball-milling conditions,
see: (a) Z. Zhang, Y.-W. Dong, G.-W. Wang and K. Komatsu,
Synlett, 2004, 61; (b) Z. Zhang, G.-W. Wang, C.-B. Miao, Y.-W. Dong
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(e) X.-L. Wu, J.-J. Xia and G.-W. Wang, Org. Biomol. Chem., 2008, 6,
548; (f) J. Gao and G.-W. Wang, J. Org. Chem., 2008, 73, 2955;
(g) G.-W. Wang, Y.-W. Dong, P. Wu, T.-T. Yuan and Y.-B. Shen, J. Org.
Chem., 2008, 73, 7088; (h) G.-W. Wang and J. Gao, Org. Lett., 2009, 11,
2385.
Acknowledgements
We are grateful for the financial support from the Knowledge
Innovation Project of the Chinese Academy of Sciences
(KJCX2.YW.H16), NSFC (20772117, 91021004) and National
Basic Research Program of China (2011CB921402).
13 For selected examples in other groups, see: (a) V. P. Balema, J.
W. Wiench, M. Pruski and V. K. Pecharsky, J. Am. Chem. Soc., 2002,
124, 6244; (b) B. Rodríguez, T. Tantanen and C. Bolm, Angew. Chem.,
Int. Ed., 2006, 45, 6924; (c) F. Schneider and B. Ondruschka, Chem-
SusChem, 2008, 1, 622; (d) R. Thorwirth, A. Stolle and B. Ondruschka,
Green Chem., 2010, 12, 985; (e) W. C. Shearouse, C. M. Korte and
J. Mack, Green Chem., 2011, 13, 598; (f) F. Ravalico, S. L. James and J.
S. Vyle, Green Chem., 2011, 13, 1778.
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1130 | Green Chem., 2012, 14, 1125–1131
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