4
Tetrahedron Letters
1. (a) Olah, G. A. Friedel-Crafts and Related Reactions; Wiley-
29. Preparation of acetamide/SO2Cl2 reagent: Acetamide/SO2Cl2
reagent is prepared by mixing the calculated amounts (1:1) of
acetamide and SO2Cl2 were added to acetonitrile solvent in a
round bottomed flask and stirred at chilled (-5oC) conditions for
about 30-45min.
Interscience: New York, 1964; Vol. III. (b). Olah, G. A. Friedel
Crafts Chemistry; Wiley-Interscience: New York, 1973.
(a) Kranzlein, G. Aluminium Chloride in der Organischen Chemie,
3rd ed.; Verlag Chemie: Berlin, 1939; (b) Thomas, C. A. Anhydrous
Aluminium Chloride in Organic Chemistry; Reinhold: New York,
1961.
2.
30. Synthesis of acetophenones using acetamide/SO2Cl2 reagent under
conventional conditions: 0.01mole of organic substrate, (aromatic
compound), 0.015 mole of acetamide/SO2Cl2 reagent and
acetonitrile were taken in a previously cleaned round bottom flask
and stirred for about 4 to 6 hours at room temperature. After
completion (as confirmed by TLC), the reaction mixture is treated
with NaHCO3 solution, followed by the addition of ethyl acetate.
Organic layer was separated, dried over anhydrous Na2SO4 and
evaporated under vacuum, purified with column chromatography
using pet ether: ethyl acetate as eluent to get pure product.
Obtained products were analyzed with mass and NMR
spectroscopic methods and confirmed with earlier reports.
3.
4.
Bradlow, L. H.; Vander Werf, C. A. J. Am. Chem. Soc. 1947, 69,
662–663.
Paul, S.; Nanda, P.; Gupta, R.; Loupy, A. Synthesis. 2003, 2877–
2881
5.
6.
7.
8.
9.
Morley, J. O. Synthesis. 1977, 54–55.
Dermer, O. C.; Billmeier, R. A. J. Am. Chem. Soc. 1942, 64, 464
Hyatt, J. A.; Raynolds, P. W. J. Org. Chem. 1984, 49, 384
Bensari, A.; Zaveri, N. T. Synthesis 2003, 267–271
Yuqing, Cao.; Fangrui, Song.; Liya, Xu.; Dingxiang, Du.; Xiaojun,
Yang.; Xiangtao, Xu. Int. J. Chem.Vol. 2011, 3, 123-128
10. Ramarao, P.; Naveen; Amit Kumar.; Srinivasarao; Arulananda Babu.
Tetrahedron Lett. 2013, 54, 1738–1742
31.
Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and
Practice (Oxford University Press; NewYork). 1998.
11. Amin, Z.; Abdol, R.; Hajipour.; Leila, K.; Tetrahedron Lett. 2008,
49, 6715–6719
32.
(a) Mason, T. J.; Lorimer, J. P. “Sonochemistry: Theory,
12. (a) Lakshmi Kantam, M.; Sri Ranganath, K. V.; Sateesh, M.; Shiva
Kumar, K.; Choudary, B. M. J. of Mol. Catal A: Chemical 2005, 225,
15–20; (b) Singh, A. P.; Pandey, A. K. J. Mol. Catal. A 1997, 123,
141; (c) Pandey, A. K.; Singh, A. P. Catal. Lett. 1997, 44, 129; (d)
De Castro, C.; Primo, J.; Corma, A. J. Mol. Catal. A 1998, 134, 215.
13. (a) Izumi, Y.; Ogawa, M.; Nohara, W.; Urabe, K. Chem. Lett. 1992,
1987; (b) Kaur, J.; Kozhevnikov, I. V. Chem. Commun. 2002, 2508;
(c) Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F. Tetrahedron Lett.
2003, 44, 5343
Applications and Uses of
Ultrasound in Chemistry,” John
Wiley and Sons, New York, 1988; (b) Mason, T. J. Chemical
Society Reviews, 1997, 26(6), 443-451.
33.
34.
(a) T.G. Leighton, The Acoustic Bubble (Academic, London,
1994).; (b) Flint, E.B.; Suslick, K.S. Science, 1991, 253, 1397-
1399
(a) McNamara, W.B.; Didenko, Y.; Suslick, K.S. Sonochemistry
and Sonoluminescence, Proceedings of the NATO Advanced
Study Institute, Series C, vol 524 (Kluwer, Dordrecht, 1999).; (b)
K.S. Suslick (ed.), Ultrasound: Its Chemical, Physical, and
Biological Effects (VCH, New York, 1988)
14. Chiche, B.; Finiels, A.; Gautheir, C.; Geneste, P. J. Mol. Catal. 1987,
42, 229
15. Ranu, B. C.; Ghosh, K.; Jana, U. J. Org. Chem. 1996, 61, 9546.
16. Sarvari, M. H.; Sharghi, H. Synthesis. 2004, 2165
17. Kawamura, M.; Cui, D. M.; Shimada, S. Tetrahedron. 2006, 62,
9201–9209
35.
36.
Kappe, C. O.; Dallinger, D.; Murphree, S. S. Practical microwave
synthesis for organic chemists -Strategies, instruments, and
protocols. 1st Ed. Wiley-VCH, Verlag GmbH & Co. KGaA,
Weinheim, 2009
18. Habib, F.; Nasser, I.; Farhad, N. Tetrahedron, 2004, 60, 10843.
19. Mohammd, M. K.; Abdolhamid, A.; Ehsan, N.;azari. Tetrahedron
Lett. 2007, 48, 4199–4202
(a) Hermken, S. P. ; Ottenheijam, H.; Ress,D. Tetrahedron, 1997,
53, 5643;(b) Hayes, B. L.Aldrichimica Acta.; 2004, 37, 66
37. Synthesis of acetophenones using acetamide/SO2Cl2 (sonication):
To a centimolar aromatic compound, acetamide/SO2Cl2 reagent
(0.015mol) and acetonitrile were added in a clean round bottom
flask and clamped in a Sonicator at room temperature. After
completion of the reaction as ascertained by TLC, the work-up
procedure to obtain the products is by and large similar to the one
discuss discussed in earlier section.
20. Anna, G.; Yu. P. R.; Garlyauskayte, Lev M. Yagupolskii. Tetrahedron
Lett. 2009, 50, 446–447
21. Cyrous, O.; Kangani.; Billy, W. Day Organic let. 2008, 10(13), 2645.
22. Yoh-ichi, Matsushita.; Kazuhiro, Sugamoto.; and Takanao, Matsui.
Tetrahedron Lett. 2004, 45, 4723–4727
23. Vasant, R.; Choudhary.; Suman, K.; Jana.; Nilesh, S.; Patil.
Tetrahedron Lett. 2002, 43, 1105– 1107
24. Venkateswarlu, M.; Rajanna, K. C.; Satish Kumar, M.;
Umesh Kumar, U.; Ramgopal, S.; Saiprakash, P. K. Int. J. Org..
Chem., 2011, 1, 233-241;
38. Microwave assisted synthesis of acetophenones using
acetamide/SO2Cl2 reagent under solvent-free conditions:
To a centimolar aromatic compound, 0.015 mol acetamide/SO2Cl2
reagents were taken in a previously cleaned beaker. About 1g of
silica gel were added to the contents and mixed thoroughly with
glass rod and placed in microwave oven (CEM-908010, bench
mate model, 300W laboratory microwave reactor). After
completion of the reaction, as checked by TLC, the reaction
mixture is treated with NaHCO3 solution, followed by the same
procedure as detailed above to get pure product.
25. Rajanna, K. C.; Moazzam Ali, M.; Sana, S.; Tasneem.; Saiprakash,
P. K. J. of Dispersion Sci. and Tech. 2004, 25, 17–21
26.
(a) Venkateswarlu, M.; Satish Kumar, M. ; Ramgopal, S.;
Rajanna, K. C.; Umesh Kumar, U.; Uppalaiah, K.; Saiprakash, P.
K. Helvetica Chimica Acta. 2011, 94, 2168–2187 (b) Rajanna, K.
C.; Venkateswarlu, M.; Satish Kumar, M.; Umesh Kumar, U.;
Venkateswarlu, G.; Saiprakash.; P. K. Int. J. Chem.Kinet., 2013,
45, 69-80
39. Haile, S.M.; Johnson D.W.; Wiseman, G.H.; Bowen, H.K. J. Am.
Ceram. Soc. 1989, 72, 2004
27.
28.
(a) Bosshard, H.H.; Mory, R.; Schmid, M.; Zollinger, H.; Helv.
Chim. Acta, 1959, 42, 1653
(b) Hasserodt, U. Chem. Ber.,
1968, 101, 113 (c) Kuhle, E. Angew. Chem. Int. 1962, 1, 647
D. Singh, B. P. Rai and Vandana Singh., Asian J. Chem.; Vol. 20,
No. 8 (2008), 5857.