1520
M. Kirihara et al. / Tetrahedron 68 (2012) 1515e1520
0
.99 (9H, s), 2.55 (3H, s), 6.86 (2H, d, J¼8.8 Hz), 7.87 (2H, d,
identical to the commercial reagent (purchased from Tokyo Kasei
Kogyo).
J¼8.8 Hz).
6
.3.10. 4-Tetrahydropyran-2-yloxy acetophenone (2j)12,13. Pale yel-
ꢂ
13
ꢂ
1
References and notes
low solid, mp: 85e87 C (lit. 84e86 C). H NMR (CDCl
1.86e2.16 (6H, m), 2.55 (3H, s), 3.60e3.63 (2H, m), 5.51 (1H, t,
J¼3.05 Hz), 7.07e7.09 (2H, m), 7.91e7.93 (2H, m).
3
):
d
1. Greene, T. W.; Wuts, P. G. M. In Protective Groups in Organic Synthesis John Wiley:
New York, NY, 2006; pp 477e500; and references cited therein.
. (a) Seebach, D.; Corey, E. J. J. Org. Chem. 1975, 40, 231e237; (b) Page, P. C. B.; van
Niel, M. B.; Prodger, J. C. Tetrahedron 1989, 45, 7643e7677.
2
ꢂ
.3.11. 4-Nitroacetophenone (2k). Yellow crystals, mp: 75e79 C
6
9
ꢂ
1
3. For recent examples, see: (a) Wang, E.-C.; Wu, C.-H.; Chien, S.-C.; Chiang, W.-C.;
Kuo, Y.-H. Tetrahedron Lett. 2007, 48, 7706e7708; (b) Desai, U. V.; Pore, D. M.;
Tamhankar, B. V.; Jadhav, S. A.; Wadgaonkar, P. P. Tetrahedron Lett. 2006, 47,
8559e8561; (c) Hajipour, A. R.; Zarei, A.; Khazdooz, L.; Ruoho, A. E. Synthesis
(
lit. 75e78 C). H NMR (CDCl ): d 2.69 (3H, s), 8.12 (2H, d,
3
J¼8.7 Hz), 8.32 (2H, d, J¼8.7 Hz). This sample is identical to the
commercial reagent (purchased from Tokyo Kasei Kogyo).
2006, 1480e1484; (d) Shaterian, H.; Hadadzadeh, H. Phosphorus, Sulfur Silicon
Relat. Elem. 2006, 181, 1059e1071; (e) Moghaddam, F. M.; Boeini, H. Z.; Zar-
garani, D.; Bardajee, G. R. Synth. Commun. 2006, 36, 1093e1096; (f) Hajipour, A.
R.; Zarei, A.; Khazdooz, L.; Pourmousavi, S. A.; Ruoho, A. E. Bull. Korean Chem.
Soc. 2005, 26, 808e810; (g) Ghorbani-Vaghei, R.; Zolfigol, M. A. J. Chin. Chem.
Soc. 2005, 52, 327e330.
. (a) English, J.; Griswold, P. H. J. Am. Chem. Soc. 1945, 67, 2039e2046; (b) Meyers,
A. I.; Comins, D. L.; Roland, D. M.; Henning, R.; Shimizu, K. J. Am. Chem. Soc.
1979, 101, 7104e7105; (c) Amoo, V. E.; Bernardo, S. D.; Weigele, M. Tetrahedron
Lett. 1988, 29, 2401e2404.
6
.3.12. Benzophenone (2l). Colorless crystals, mp: 47e49 C (lit.9
ꢂ
ꢂ
1
47e51 C). H NMR (CDCl ): d 7.48e7.59 (6H, m), 7.78e7.83 (4H,
3
m). This sample is identical to the commercial reagent (purchased
from Kanto Kagaku).
4
.3.13. Benzaldehyde (2m). Colorless liquid, 1H NMR (CDCl
6
3
):
7.49e7.57 (2H, m), 7.60e7.68 (1H, m), 7.88 (2H, m), 10.03 (1H, s).
d
5
. (a) Ganguly, N. C.; Nayek, S.; Barik, S. K. J. Indian Chem. Soc. 2011, 88, 251e256;
(b) Mondal, E.; Bose, G.; Sahu, P. R.; Khan, A. T. Chem. Lett. 2001, 1158e1159.
. (a) Kirihara, M.; Okubo, K.; Koshiyama, T.; Kato, Y.; Hatano, A. ITE Lett. 2004, 5,
This sample is identical to the commercial reagent (purchased from
Nacalai Tesque).
6
279e281; (b) Kirihara, M.; Harano, A.; Tsukiji, H.; Takizawa, R.; Uchiyama, T.;
Hatano, A. Tetrahedron Lett. 2005, 46, 6377e6380; (c) Kirihara, M.; Ogawa, S.;
Noguchi, T.; Okubo, K.; Monma, Y.; Shimizu, I.; Shimosaki, R.; Hatano, A.; Hirai,
Y. Synlett 2006, 2287e2289; (d) Kirihara, M.; Asai, Y.; Ogawa, S.; Noguchi, T.;
Hatano, A.; Hirai, Y. Synthesis 2007, 3286e3289; (e) Noguchi, N.; Hirai, Y.;
Kirihara, M. Chem. Commun. 2008, 3040e3042; (f) Kirihara, M.; Yamamoto, J.;
Noguchi, T.; Hirai, Y. Tetrahedron Lett. 2009, 50, 1180e1183; (g) Kirihara, M.;
Yamamoto, J.; Noguchi, T.; Itou, A.; Naito, S.; Hirai, Y. Tetrahedron 2009, 65,
6
5
6
.3.14. Naphthalene-2-carbaldehyde (2n). Colorless crystals, mp:
ꢂ
9
ꢂ
1
9e61 C (lit. 59e63 C). H NMR (CDCl
3
):
d
7.63 (2H, td, J¼22.9,
.8 Hz), 7.90e8.03 (4H, m), 8.35 (1H, s), 10.17 (1H, s). This sample is
identical to the commercial reagent (purchased from Kanto
Kagaku).
10477e10484; (h) Kirihara, M.; Itou, A.; Noguchi, T.; Yamamoto, J. Synlett 2010,
1
557e1561.
1
6
.3.15. Octanal (2o). Colorless liquid, H NMR (CDCl
3
):
d
0.87 (3H, t,
7. Black, J. Clin. Mater. 1994, 16, 167e173.
J¼5.0 Hz), 1.26e1.32 (10H, m), 1.61e1.66 (2H, m), 2.42 (2H, dt, J¼7.4,
.8 Hz), 9.76 (1H, s). This sample is identical to the commercial
reagent (purchased from Tokyo Kasei Kogyo).
8. Marshall, J. A.; Belletire, J. L. Tetrahedron Lett. 1971, 12, 871e874.
9
. ALDRICH Chemistry, Handbook of Fine Chemistry; Sigma-Aldrich: St. Louis, 2009.
0. D’Sa, B.; McLeod, D.; Verkade, J. G. J. Org. Chem. 1997, 62, 5057e5061.
1. Heath, W. H.; Palmieri, F.; Adams, J. R.; Long, B. K.; Chute, J.; Holcombe, T. W.;
1
1
1
Zieren, S.; Truitt, M. J.; White, J. L.; Willson, C. G. Macromolecules 2008, 41,
719e726.
2. Semwal, A.; Nayak, S. K. Synthesis 2005, 71e74.
3. Dimmock, J. R.; Shyam, K.; Logan, B. M.; Smith, P. J.; Cross, B. M. J. Pharm. Sci.
1984, 73, 471e477.
6
(
1
.3.16. Cyclohexanecarbaldehyde (2p). Colorless liquid, 1H NMR
CDCl ): 1.20e1.43 (5H, m), 1.62e1.68 (1H, m), 1.72e1.79 (2H, m),
.84e1.93 (2H, m), 2.19e2.29 (1H, m), 9.62 (1H, s). This sample is
1
1
3
d