1808
A. K. Chakraborti et al.
LETTER
(13) Chauhan, K. K.; Frost, C. G.; Love, I.; Waite, D. Synlett
Finally, it may be mentioned that perchlorates are poten-
tially explosive when heated in the presence of
combustible substances at high temperature29 and there-
fore care should be taken while handling perchlorates un-
der such conditions. However, some perchlorate salts
have high thermal stability.30 For example, LiClO4 is
thermally stable at or above its melting point of 247 °C
and can be dried under vacuum at 160 °C for prolonged
period (ca 50 h).31 Exposure to nominal levels of
perchlorate does not adversely affect the health and safe-
ty.30 Thus, in the present work the requirement of catalytic
quantities of BiOClO4·xH2O, operation in the absence of
combustible substances (e.g. solvent), and mild reaction
conditions (room temperature) should circumvent the
problem of potential hazard associated with perchlorates
and make the methodology suitable for industrial
application.
1999, 1743.
(14) (a) Orita, A.; Tanahashi, C.; Kakuda, A.; Otera, J. Angew.
Chem. Int. Ed. 2000, 39, 2877. (b) Orita, A.; Tanahashi, C.;
Kakuda, A.; Otera, J. J. Org. Chem. 2001, 66, 8926.
(c) Carrigan, M. D.; Freiberg, D. A.; Smith, R. C.; Zerth, H.
M.; Mohan, R. S. Synthesis 2001, 2091.
(d) Mohammadpoor-Baltork, I.; Aliyan, H.; Khosropour, A.
R. Tetrahedron 2001, 57, 5851.
(15) Kumareswaran, R.; Pachamuthu, K.; Vankar, Y. D. Synlett
2000, 1652.
(16) Kumar, P.; Pandey, R. K.; Bodas, M. S.; Dongare, M. K.
Synlett 2001, 206.
(17) Nakae, Y.; Kusaki, I.; Sato, T. Synlett 2001, 1584.
(18) Bartoli, G.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.;
Massaccesi, M.; Rinaldi, S.; Sambri, L. Synlett 2003, 39.
(19) Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Procopio, A.;
Nardi, M.; Bartoli, G.; Romeo, R. Tetrahedron Lett. 2003,
44, 5621.
(20) (a) Sweet, D. V. Registry of Toxic Effects of Chemical
Substances, 1985-86; U. S. Govt. Printing Office:
Washington DC, 1988, 3336. (b) Sweet, D. V. Registry of
Toxic Effects of Chemical Substances, 1985-86; U. S. Govt.
Printing Office: Washington DC, 1988, 4049.
(21) Buckler, S. A. J. Am. Chem. Soc. 1962, 84, 3093.
(22) Olah, G. A.; Prakash, G. K. S. Superacids; Wiley: New
York, 1985.
Acknowledgement
Shivani thanks CSIR, New Delhi for the award of Junior Research
Fellowship.
References
(23) Chakraborti, A. K.; Gulhane, R. Tetrahedron Lett. 2003, 44,
3521.
(24) Chakraborti, A. K.; Gulhane, R. Chem. Commun. 2003,
1896.
(1) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic
Synthesis, 3rd ed.; Wiley: New York, 1999.
(2) (a) Chakraborti, A. K.; Nayak, M. K.; Sharma, L. J. Org.
Chem. 2002, 67, 1776. (b) Chakraborti, A. K.; Nayak, M.
K.; Sharma, L. J. Org. Chem. 2002, 67, 2541.
(c) Chakraborti, A. K.; Sharma, L.; Sharma, U. Tetrahedron
2001, 57, 9343. (d) Chakraborti, A. K.; Nayak, M. K.;
Sharma, L. J. Org. Chem. 1999, 64, 8027.
(3) Steglich, W.; Höfle, G. Angew. Chem., Int. Ed. Engl. 1969,
8, 981.
(4) (a) Vedejs, E.; Diver, S. T. J. Am. Chem. Soc. 1993, 115,
3358. (b) Vedejs, E.; Bennet, N. S.; Conn, L. M.; Diver, S.
T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org.
Chem. 1993, 58, 7286.
(5) (a) Ahmad, S.; Iqbal, J. Tetrahedron Lett. 1986, 27, 3791.
(b) Ahmad, S.; Iqbal, J. Chem. Commun. 1987, 114.
(c) Iqbal, J.; Srivastava, R. R. J. Org. Chem. 1992, 57, 2001.
(6) (a) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J.
Am. Chem. Soc. 1995, 117, 4413. (b) Ishihara, K.; Kubota,
M.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1996, 61,
4560.
(7) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265.
(8) (a) Procopiou, P. A.; Baugh, S. P. D.; Flack, S. S.; Inglis, G.
G. A. Chem. Commun. 1996, 2625. (b) Procopiou, P. A.;
Baugh, S. P. D.; Flack, S. S.; Inglis, G. G. A. J. Org. Chem.
1998, 63, 2342.
(25) Schilt, A. A. Perchloric Acid and Perchlorates; GFS
Chemicals Publications: Columbus OH, 1979, 17.
(26) (a) Yatsimirksii, K. B.; Vasil’ev, V. P. Instability Constants
of Complex Compounds; Pergamon: Elmsford N. Y., 1960.
(b) Bjerrum, J.; Schwarzenbach, G.; Sillen, L. G. Stability
Constants of Metal-Ion Complexes: Part II, Inorganic
Ligands; The Chemical Society: London, 1958.
(27) Typical procedure for acetylation: 2-Hydroxynaphthalene
(360 mg, 2.5 mmol) was treated with Ac2O (0.24 mL, 2.5
mmol) under neat conditions at r.t. for 30 min (monitored by
GCMS) under magnetic stirring in the presence of
BiOClO4·xH2O (8.11 mg, 0.025 mmol, 1 mol%). The
reaction mixture was diluted with Et2O (50 mL) and filtered
through a cotton plug to separate the catalyst. The filtrate
was washed successively with 2% aq NaOH (15 mL), brine
(15 mL), dried (NaSO4) and concentrated to afford the
product (442 mg, 95%), which was in full agreement with
the spectral data (mp, IR, 1H NMR and EIMS) of an
authentic sample of 2-acetoxynaphthalene. In most of the
cases the products gave satisfactorily spectral (IR, 1H NMR
and MS) data without any further purification. Wherever
applicable, purification was done through crystallization (for
solid) or passing through a column of silica gel (for liquid)
and eluting with 5% Et2O in hexane.
(9) Li, A.-X.; Li, T.-S.; Ding, T.-H. Chem. Commun. 1997,
1389.
(10) Chandrasekhar, S.; Ramachander, T.; Takhi, M.
Tetrahedron Lett. 1998, 39, 3263.
(11) Ballini, R.; Bosica, G.; Carloni, S.; Ciaralli, L.; Maggi, R.;
Sartori, G. Tetrahedron Lett. 1998, 39, 6049.
(12) (a) Saravanan, P.; Singh, V. K. Tetrahedron Lett. 1999, 40,
2611. (b) Chandra, K. L.; Sarvanan, P.; Singh, R. K.; Singh,
V. K. Tetrahedron 2002, 58, 1369.
(28) Garrett, R. L. In Designing Safer Chemicals; Garrett, R. L.;
De Vito, S. C., Eds.; American Chemical Society
Symposium Series 640: Washington DC, 1996, Chap. 1.
(29) Schumacher, J. C. Perchlorates - Their Properties,
Manufacture and Uses; ACS Monograph Series, Reinhold:
New York, 1960.
(30) Long, J. Chem. Health Saf. 2002, 9, 12.
(31) Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc.
1990, 112, 4595.
Synlett 2003, No. 12, 1805–1808 © Thieme Stuttgart · New York