R. Umeda et al. / Tetrahedron 67 (2011) 7217e7221
7221
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(68 MHz, CDCl3)
22.6, 13.9, 11.8. IR (KBr) 2959, 2873, 1732, 1460, 1171 cmꢁ1
Compound 5l: 1H NMR (270 MHz, CDCl3)
7.98 (d, J¼7.0 Hz, 2H),
7.54e7.24 (m, 8H), 4.53e4.41 (m, 2H), 3.56e3.48 (m,1H), 3.42e3.29
(m, 2H), 2.46e2.05 (m, 2H). 13C NMR (100 MHz, CDCl3)
166.4,
139.9, 133.0, 128.8, 128.4, 127.9, 127.3, 68.3, 42.5, 42.2, 35.3.
Compound 8: 1H NMR (CDCl3, 400 MHz):
8.04e8.01 (m, 2H),
7.61e7.57 (m, 1H), 7.48e7.44 (m, 2H), 4.31 (s, 2H), 3.68e3.62 (m,
4H), 1.22 (s, 3H). 13C NMR (CDCl3, 100 MHz):
165.9, 133.3, 129.5,
129.4, 128.4, 66.7, 48.0, 41.0, 18.8. IR (KBr): 3063, 2975, 1724, 1451,
1272, 1111, 710 cmꢁ1
d 176.4, 63.1, 47.4, 44.4, 31.8, 29.6, 29.2, 26.1, 25.4,
.
d
d
d
d
.
Acknowledgements
This research was supported by a Grant-in-Aid for Science Re-
search, and Strategic Project to Support the Formation of Research
Bases at Private Universities from the Ministry of Education, Culture
Sports, Science and Technology of Japan.
9. Selected papers on using ReBr(CO)5 as catalyst for CeC bond formation, see: (a)
Zuo, W.-X.; Hua, R.; Qiu, X. Synth. Commun. 2004, 34, 3219; (b) Kuninobu, Y.;
Kawata, A.; Takai, K. Org. Lett. 2005, 7, 4823; (c) Zuo, W.-X.; Hua, R. Tetrahedron
Lett. 2007, 63, 11803; (d) Kuninobu, Y.; Yu, P.; Takai, K. Chem. Lett. 2007, 36, 1162.
ꢀ
ꢁꢀ
10. Vícha, R.; Necas, M.; Potacek, M. Collect. Czech. Chem. Commun. 2006, 71, 709.
11. Sinha et al. have reported that Re2O7 catalyzed hetero acylative ring-opening
dimerization of THF with trifluoroacetic anhydride and a carboxylic acid at
room temperature, see: Lo, H. C.; Han, H.; D’Souza, L. J.; Sinha, S. C.; Keinan, E. J.
Am. Chem. Soc. 2007, 129, 1246.
Supplementary data
Supplementary data for new compounds of 1H and 13C NMR
spectra. Supplementary data can be found in the online version, at
12. It has already known that rhenium complexes, such as CH3ReO3 and Re2O7, act
~
€
as Lewis acids. For a related review, see: Romao, C. C.; Kuhn, F. E.; Herrmann,
W. A. Chem. Rev. 1997, 97, 3197.
13. Takahashi, Y.; Yoneda, N. Synth. Commun. 1989, 19, 1945.
14. Gotoh, H.; Masui, R.; Ogino, H.; Shouji, M.; Hayashi, Y. Angew. Chem., Ed. 2006,
45, 6853.
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