K. Rajender Reddy et al. / Tetrahedron Letters 50 (2009) 2050–2053
2053
4. (a) Chen, F.-E.; Li, Y.-Y.; Xu, M.; Jia, H.-Q. Synthesis 2002, 1804–1806; (b)
Iranpoor, N.; Firouzabadi, H.; Akhlaghinia, B.; Nowrouzi, N. J. Org. Chem. 2004,
69, 2562–2564; (c) Mori, N.; Togo, H. Synlett 2005, 1456–1458.
14. (a) Yamazaki, S.; Yamazaki, Y. Bull. Chem. Soc. Jpn. 1990, 63, 301–303; (b)
Biondini, D.; Brinchi, L.; Germani, R.; Goracci, L.; Savelli, G. Eur. J. Org. Chem.
2005, 3060–3063.
5. (a) Toland, W. G. J. Org. Chem. 1962, 27, 869–871; (b) Gelas-Mialhe, Y.; Vessiere,
R. Synthesis 1980, 1005–1007; (c) Das, B.; Madhusudhan, P.; Venkataiah, B.
Synlett 1999, 1569–1570; (d) Karmarkar, S. N.; Kelkar, S. L.; Wadia, M. S.
Synthesis 1985, 510–512; (e) Miller, M. J.; Loudon, G. M. J. Org. Chem. 1975, 40,
126–127; (f) Smith, R. F.; Walker, L. E. J. Org. Chem. 1962, 27, 4372–4375; (g)
Arote, N. D.; Bhalerao, D. S.; Akamanchi, K. G. Tetrahedron Lett. 2007, 48, 3651–
3653; (h) Sharghi, H.; Hosseini Sarvari, M. Tetrahedron 2002, 58, 10323–10328;
(i) Carmeli, M.; Shefer, N.; Rozen, S. Tetrahedron Lett. 2006, 47, 8969–8972; (j)
Movassagh, B.; Shokri, S. Tetrahedron Lett. 2005, 46, 6923–6925; (k) Wang, E. C.;
Lin, G. J. Tetrahedron Lett. 1998, 39, 4047–4050; (l) Ballini, R.; Fiorini, D.;
Plamieri, A. Synlett 2003, 1841–1843; (m) Bandgar, B. P.; Makone, S. S. Synlett
2003, 262–264; (n) Hwu, J. R.; Wong, F. F. Eur. J. Org. Chem. 2006, 2513–2516.
6. (a) Huber, V. J.; Bartsch, R. A. Tetrahedron 1998, 54, 9281–9288; (b) Mlinaric´-
Majerski, K.; Margeta, R.; Veljkovic´, J. Synlett 2005, 2089–2091; (c) Kangani, C.
O.; Day, B. W.; Kelley, D. E. Tetrahedron Lett. 2007, 48, 5933–5937; (d) Telvekar,
V. N.; Rane, R. A. Tetrahedron Lett. 2007, 48, 6051–6053.
7. (a) Mori, K.; Yamaguchi, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Chem. Commun.
2001, 461–462; (b) Chen, F. E.; Peng, Z. Z.; Fu, H.; Liu, J. D.; Shao, L. Y. J. Chem.
Res. (S) 1999, 726–727; (c) Iida, S.; Togo, H. Synlett 2007, 407–410; (d) Iida, S.;
Togo, H. Synlett 2006, 2633–2635; (e) De luca, L.; Giacomelli, G. Synlett 2004,
2180–2184; (f) Chen, F. E.; Kuang, Y. Y.; Dai, H. F.; Lu, L.; Huo, M. Synthesis 2003,
2629–2631.
8. (a) Yamazaki, S.; Yamazaki, Y. Chem. Lett. 1990, 571–574; (b) Chen, F.; Li, Y.; Xu,
M.; Jia, H. Synthesis 2002, 1804–1806; (c) McAllister, G. D.; Wilfred, C. D.;
Taylor, R. J. K. Synlett 2002, 1291–1292; (d) Iida, S.; Togo, H. Tetrahedron 2007,
63, 8274–8281.
15. Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc. Chem. Commun. 1978,
562.
16. (a) Shroder, M.; Griffith, W. P. J. Chem. Soc. Chem. Commun. 1979, 58–59; (b)
Green, G.; Griffith, W. P.; Hollinshead, D. M.; Ley, S. V.; Schroder, M. J. Chem.
Soc., Perkin Trans. I 1984, 681–686.
17. Cenini, S.; Porta, F.; Pizzottio, M. J. Mol. Catal. 1982, 15, 297–308.
18. Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2003, 42, 1480.
19. Feldhues, U.; Schafer, H. J. Synthesis 1982, 145.
20. (a) Semmelhack, M. F.; Schmid, C. R. J. Am. Chem. Soc. 1983, 105, 6732–6734; (b)
Shono, T.; Matsumura, Y.; Inoue, K. J. Am. Chem. Soc. 1984, 106, 6075–6076.
21. Togo, H.; Iida, S. Synlett 2006, 2159–2175. and references cited therein.
22. Reddy, K. R.; Maheswari, C. U.; Venkateshwar, M.; Kantam, M. L. Eur. J. Org.
Chem. 2008, 3619–3622.
23. General procedure for the synthesis of nitriles from alcohols: To a solution of
alcohol (1.0 mmol), potassium iodide (0.05 mmol) in 3 mL of aq NH3 was
added, a solution of 70% aqueous TBHP (3.8 mmol) was added dropwise over a
period of 30 min and stirred at 60 °C. Progress of the reaction was monitored
by TLC. After completion of the reaction, the mixture was quenched with
saturated aqueous Na2S2O3, washed with brine, extracted with ethyl acetate
and dried over anhydrous Na2SO4. Removal of the solvent under vacuum
afforded the crude product, which was purified by column chromatography
using hexane/ethyl acetate (9:1) mixture and was analyzed by 1H NMR, GC and
GC–MS. Similar procedure was followed for synthesis of nitriles from
aldehydes but with lesser amount of TBHP (2.2 mmol).
24. (a) Yamada, S.; Morizono, D.; Yamamoto, K. Tetrahedron Lett. 1992, 33, 4329–
4332; (b) Barluenga, J.; Marco-Arias, M.; Gonzalez-Bobes, F.; Ballesteros, A.;
Gonzalez, J. M. Chem. Commun. 2004, 2616–2617.
9. Nakagawa, K.; Tsuji, T. Chem. Pharm. Bull. 1963, 11, 296.
10. (a) Karnetani, T.; Takahashi, T.; Ohsawa, T.; Ihara, M. Synthesis 1977, 245; (b)
Jallabert, C.; Rivikre, H. Tetrahedron Lett. 1977, 18, 1215–1218; (c) Capdevielle,
P.; Lavigne, A.; Maumy, M. Synthesis 1989, 453–454; (d) Yamaguchi, J.; Takeda,
T. Chem. Lett. 1992, 1933–1937.
11. (a) Clarke, T. G.; Hampson, N. A.; Lee, J. B.; Morley, J. R.; Scanlon, B. Tetrahedron
Lett. 1968, 9, 5685–5688; (b) Lee, J. B.; Parkin, C.; Shaw, M. J.; Hampson, N. A.;
MacDonald, K. I. Tetrahedron 1973, 29, 751–752.
12. Belew, J. S.; Garza, C.; Mathieson, J. W. J. Chem. Soc., D 1970, 634–635.
13. (a) Mihailovic, M. L.; Andrejevic, V.; Stojiljkovic, A. Tetrahedron Lett. 1965, 48,
461–463; (b) Stojiljkovic, A.; Andrejevic, V.; Mihailovic, M. L. Tetrahedron 1967,
23, 721–732.
25. Gram scale preparation of 4-methoxy benzonitrile: To a suspension of alcohol
(5.0 g, 36.2 mmol) in 115 mL of aq NH3 was added KI (20 mol %), and a solution
of 70% aqueous TBHP (3.8 equiv) was added dropwise over a period of 30 min
and stirred at 60 °C. Progress of the reaction was monitored by TLC. After
completion of the reaction (24 h), the mixture was quenched with saturated
aqueous Na2S2O3, washed with brine, extracted with ethyl acetate and dried
over anhydrous Na2SO4. Removal of the solvent under vacuum afforded the
crude product.