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PAPER
(E)-(3-Chloroprop-1-en-1-yl)benzene (4e)
11, 4608. (g) Vieira, T. O.; Meaney, L. A.; Shi, Y.-L.; Alper,
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(b) Coste, A.; Karthikeyan, G.; Couty, F.; Evano, G. Angew.
Chem. Int. Ed. 2009, 48, 4381. For a review featuring the
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Manabe, K. Synthesis 2009, 1405.
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Soc. 1962, 84, 1745. (b) Fang, Y.-Q.; Lifchits, O.; Lautens,
M. Synlett 2008, 413.
General procedure B was followed (1 mmol scale). The product was
purified by flash column chromatography (silica gel, pentane); this
provided 4e as a colorless oil. Characterization data matched those
of commercially available material.
Yield: 122 mg (80%).
1H NMR (400 MHz, CDCl3): d = 7.23–7.41 (m, 5 H), 6.65 (d,
J = 15.6 Hz, 1 H), 6.26–6.36 (m, 1 H), 4.24 (d, J = 8.3 Hz, 2 H).
13C NMR (100 MHz, CDCl3): d = 135.9, 134.2, 128.7, 128.3,
126.8, 125.0, 45.5.
(7) (a) Minato, A.; Suzuki, K.; Tamao, K. J. Am. Chem. Soc.
1987, 109, 1257. (b) Tan, Z.; Negishi, E. Angew. Chem. Int.
Ed. 2006, 45, 762. (c) Shi, J.; Zeng, X.; Negishi, E. Org.
Lett. 2003, 5, 1825. (d) Fang, Y.-Q.; Yuen, J.; Lautens, M.
J. Org. Chem. 2007, 72, 5152. (e) Liron, F.; Fosse, C.;
Pernolet, A.; Roulland, E. J. Org. Chem. 2007, 72, 2220.
(f) Cantet, A.-C.; Gesson, J.-P.; Renoux, B.; Jouannetaud,
M.-P. Tetrahedron Lett. 2007, 48, 5255. (g) Minato, A.
J. Org. Chem. 1991, 56, 4052. (h) Christopher, A.; Brandes,
D.; Kelly, S.; Minehan, T. Org. Lett. 2006, 8, 451.
(8) Rabinowitz, R.; Marcus, R. J. Am. Chem. Soc. 1962, 84,
1312.
(9) (a) Speziale, A. J.; Marco, G. J.; Ratts, K. W. J. Am. Chem.
Soc. 1960, 82, 1260. (b) Speziale, A. J.; Ratts, K. W. J. Am.
Chem. Soc. 1962, 84, 854. (c) Vinczer, P.; Struhar, S.;
Novak, L.; Szantay, C. Tetrahedron Lett. 1992, 33, 683.
(d) Aggarwal, V.; Mereu, A. J. Org. Chem. 2000, 65, 7211.
(e) Shastin, A. V.; Korotchenko, V. N.; Nenajdenko, V. G.;
Balenkova, E. S. Tetrahedron 2000, 56, 6557. (f) Rezaei,
H.; Normant, J. F. Synthesis 2000, 109. (g) Hosomi, A.;
Inaba, M.; Sakurai, H. Tetrahedron Lett. 1983, 24, 4727.
(h) Wang, Z.; Campagna, S.; Xu, G.; Pierce, M. E.;
Fortunak, J. M.; Confalone, P. N. Tetrahedron Lett. 2000,
41, 4007. (i) Seyferth, D.; Marmor, R. S. J. Organomet.
Chem. 1973, 59, 237. (j) Takeda, T.; Endo, Y.; Reddy, A. C.
S.; Sasaki, R.; Fujiwara, T. Tetrahedron 1999, 55, 2475.
(k) Li, J.; Xu, X.; Zhang, Y. Tetrahedron Lett. 2003, 44,
9349.
2-Chloro-1,2-bis(4-methoxyphenyl)ethanone (4f)
General procedure B was followed (1 mmol scale). The product was
purified by recrystallization from Et2O–pentane; this provided 4f as
a white solid. Characterization data perfectly match the previously
reported 1H and 13C NMR data.8 However, the authors reported the
substrate to be a colorless oil.8 We find this surprising, since the cor-
responding diphenylethanone has been reported to be a solid that
melts at 64–65 °C.17
Yield: 215 mg (74%); mp 70–71 °C (Lit.8 oil).
1H NMR (400 MHz, CDCl3): d = 7.94 (d, J = 9.0 Hz, 2 H), 7.40 (d,
J = 8.7 Hz, 2 H), 6.85–6.92 (m, 4 H), 6.29 (s, 1 H), 3.84 (s, 3 H),
3.79 (s, 3 H).
13C NMR (100 MHz, CDCl3): d = 190.0, 163.9, 160.2, 131.5,
130.5, 129.9, 128.3, 127.2, 114.6, 114.0, 62.1, 55.6, 55.4.
Supporting Information for this article is available online at
Acknowledgment
We gratefully acknowledge the financial support from the Natural
Sciences and Engineering Research Council of Canada (NSERC),
the University of Toronto, and Merck-Frosst Canada for an Indus-
trial Research Chair. S.G.N. thanks NSERC for a postgraduate
scholarship.
(10) (a) Clement, B. A.; Soulen, R. L. J. Org. Chem. 1976, 41,
556. The application of this procedure on cyclohexanones
and a-methoxyimino b-keto esters has been reported. See:
(b) Burton, G.; Elder, J. S.; Fell, S. C. M.; Stachulski, A. V.
Tetrahedron Lett. 1988, 29, 3003.
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Prices in USD from Sigma-Aldrich, October 2010.
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Synthesis 2011, No. 2, 342–346 © Thieme Stuttgart · New York