D. Chaturvedi et al. / Tetrahedron Letters 48 (2007) 5043–5045
5045
13. (a) Oi, S.; Kuroda, Y.; Matsuno, S.; Inoue, Y. Bull. Chem.
Soc. Jpn. 1993, 8, 985; (b) Dixneuf, P. H.; Bruneau, C. J.
Mol. Catal. 1992, 74, 97–101.
14. (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205–
6207; (b) Salvatore, R. N.; Flanders, V. L.; Ha, D.; Jung,
K. W. Org. Lett. 2000, 2, 2797–2800; (c) Verdecchia, M.;
Feroci, M.; Palombi, L.; Rossi, L. J. Org. Chem. 2002, 67,
8287–8289.
Acknowledgements
The authors thank Dr. Nitya Anand for his fruitful sug-
gestions and the SIAF division of CDRI for providing
spectroscopic and analytical data.
References and notes
15. (a) Casadei, M. A.; Cesa, S.; Feroci, M.; Inesi, A.; Rossi,
L.; Moracci, F. M. Tetrahedron 1997, 53, 167–176; (b)
Casadei, M. A.; Inesi, A.; Rossi, L. Tetrahedron Lett.
1997, 38, 3565–3568.
1. (a) Shaikh, A. G.; Sivaram, S. Chem. Rev. 1996, 96, 951–
976; (b) Parrish, J. P.; Salvatore, R. N.; Jung, K. W.
Tetrahedron 2000, 56, 8207–8237.
2. (a) Avramova, P.; Dryanovska, L.; Ilarionov, Y. Pharma-
zie 1977, 32, 201; (b) Kawaguchi, T.; Nakano, M.; Juni,
K.; Inoue, S.; Yoshida, Y. Chem. Pharm. Bull. 1983, 31,
1400–1412; (c) Avramova, P.; Dryanovska, L.; Ilarionov,
Y. Pharmazie 1983, 38, 443; (d) Holas, T.; Vavrova, K.;
Sima, M.; Klimentova, J.; Hravalek, A. Bioorg. Med.
Chem. 2006, 14, 7671–7680.
3. (a) Berlicki, L.; Kafarski, P. Curr. Org. Chem. 2005, 9,
1829–1850; (b) Woznica, Z.; Adamczewski, K.; Heller, K.
Progr. Plant Protection 2005, 45, 524–532; (c) Alen, J.;
Bustillo, A. J.; Hernandez-Galan, R.; Collado, I. G. Curr.
Org. Chem. 2006, 10, 2037–2054.
16. (a) Kawanami, H.; Sasaki, A.; Matsui, K.; Ikushima, Y.
Chem. Commun. 2003, 896–897; (b) Tian, J. S.; Wang, J.
Q.; Chen, J. Y.; Fan, J. G.; Cai, F.; He, L. N. Appl. Catal.,
A 2006, 301, 215–221.
17. (a) Yamaguchi, K.; Ebitani, K.; Yoshida, T.; Yoshida, H.;
Kaneda, K. J. Am. Chem. Soc. 1999, 121, 4526; (b)
Sakakura, T.; Saito, Y.; Okano, M.; Choi, J.-C.; Sako, T.
J. Org. Chem. 1998, 63, 7095; (c) Sakakura, T.;
Choi, J.-C.; Saito, Y.; Masuda, T.; Sako, T.; Oriyama,
T. J. Org. Chem. 1999, 64, 4506; (d) Choi, J.-C.; Sakakura,
T.; Sako, T. J. Am. Chem. Soc. 1999, 121, 3793–
3794.
4. (a) Butler, C. L.; Renfrew, A. G. J. Am. Chem. Soc. 1938,
60, 1473; (b) Morgan, M. S.; Gretcher, L. H. J. Am. Chem.
Soc. 1946, 68, 781–782; (c) Andriamialisoa, R. Z.; Lang-
lois, N.; Langlois, Y. J. Org. Chem. 1985, 50, 961.
5. Greene, T. W.; Wuts, P. G. M. Protective Groups in
Organic Synthesis, 2nd ed.; John Wiley and Sons: New
York, 1991; pp 104–110, 140–141, 165–167, 173–174.
6. (a) Mertes, M. P.; Coats, E. A. J. Med. Chem. 1969, 12,
154–163; (b) Jones, D. S.; Tittensor, J. R. J. Chem. Soc.,
Chem. Commun. 1969, 1240–1241; (c) Tittensor, J. R. J.
Chem. Soc. 1971, 2656–2660.
7. Abrams, E. Carbonic and Chloroformic Esters. In Kirk-
Othmer Encyclopedia of Chemical Technology, 3rd ed.;
John Wiley and Sons: New York, 1978; Vol. 4, pp 758–771.
8. (a) Schwartz, S. S.; Goodman, S. H. Plastics Materials and
Processes; Van Nostrand Reinhold: New York, 1982; p
254; (b) Darensbourg, D. J.; Niezgoda, S. A.; Draper, J.
D.; Reibenspies, J. H. J. Am. Chem. Soc. 1998, 120, 4690–
4691; (c) Bisht, K. S.; Svirkin, Y. Y.; Henderson, L. A.;
Gross, R. A.; Kaplan, D. L.; Swift, G. Macromolecules
1997, 30, 7735–7740; (d) Al-Azemi, T. F.; Bishit, K. S.
Macromolecules 1999, 32, 6536–6541; (e) Golden, J. H.;
Chew, B. G. M.; Zax, D. B.; Disalvo, F. J.; Frechet, J. M.
J.; Tarascon, J.-M. Macromolecules 1995, 28, 3468.
9. (a) Pacheco, M. A.; Marshall, C. L. Energy Fuels 1997, 11,
2; (b) Ishida, N.; Hasegawa, H.; Sasaki, U.; Ishikawa, T.
US Patent 5,391,311, 1995; (c) Ishida, N.; Sakamoto, T.;
Hasegawa, H. US Patent 5,370,809, 1994.
18. (a) Chaturvedi, D.; Kumar, A.; Ray, S. Synth. Commun.
2002, 32, 2651–2656; (b) Chaturvedi, D.; Ray, S. Lett.
Org. Chem. 2005, 2, 742–744; (c) Chaturvedi, D.; Ray, S.
J. Sulfur Chem. 2005, 26, 365–371; (d) Chaturvedi, D.;
Ray, S. Monatsh. Chem. 2006, 137, 201–206; (e) Chaturv-
edi, D.; Ray, S. Monatsh. Chem. 2006, 137, 311–317; (f)
Chaturvedi, D.; Ray, S. Monatsh. Chem. 2006, 137, 459–
463; (g) Chaturvedi, D.; Ray, S. Monatsh. Chem. 2006,
137, 465–469; (h) Chaturvedi, D.; Ray, S. J. Sulfur Chem.
2006, 27, 65–270; (i) Chaturvedi, D.; Ray, S. Monatsh.
Chem. 2006, 137, 1219–1223; (j) Chaturvedi, D.; Mishra,
N.; Mishra, V. Monatsh. Chem. 2007, 138, 57–60; (k)
Chaturvedi, D.; Mishra, N.; Mishra, V. Chin. Chem. Lett.
2006, 17, 1219–1223; (l) Chaturvedi, D.; Mishra, N.;
Mishra, V. J. Sulfur Chem. 2007, 28, 39–44.
19. (a) Chaturvedi, D.; Kumar, A.; Ray, S. Tetrahedron Lett.
2003, 44, 7637–7639; (b) Chaturvedi, D.; Ray, S. Tetra-
hedron Lett. 2006, 47, 1307–1309; (c) Chaturvedi, D.; Ray,
S. Tetrahedron Lett. 2007, 48, 149–151.
20. Typical experimental procedure: Dibenzyl carbonate
(entry 1): Benzyl alcohol (1 ml, 9 mmol) was taken in
dry DMSO (35 ml) and gaseous CO2 was bubbled through
it for 30 min. To this, a mixture of triphenylphosphine
(2.2 g, 9 mmol) and diethyl azodicarboxylate (1.33 ml,
9 mmol) was added slowly in 2–3 small portions. Next,
benzyl alcohol (1 ml, 9 mmol) was added. The reaction
was stirred until completion (5 h) as confirmed by TLC.
The reaction mixture was then poured into distilled water
(50 ml) and extracted with ethyl acetate thrice. The
organic layer was separated and dried over anhydrous
sodium sulphate and then concentrated to afford dibenzyl
carbonate as an oil (2.06 g, 90%). IR (neat): 1750 (C@O)
10. (a) Burk, R. M.; Roof, M. B. Tetrahedron Lett. 1993, 34,
395–399; (b) Choppin, A. R.; Rogers, J. W. J. Am. Chem.
Soc. 1948, 70, 2967–2968; (c) Bertolini, G.; Gianfranco, P.;
Vergani, B. J. Org. Chem. 1998, 63, 6031–6032.
11. (a) Matzner, M.; Kurkjy, R. P.; Cotter, R. J. Chem. Rev.
1965, 65, 645; (b) Arime, T.; Tsurumaki, Y.; Mori, N.
Chem. Express 1993, 8, 377.
12. (a) Graziani, M.; Uguagliati, P.; Carturan, G. J. Organo-
met. Chem. 1971, 27, 275; (b) Hallgreeen, J. E.; Matthews,
R. O. J. Organomet. Chem. 1979, 175, 135; (c) Fenton, D.
M.; Steinwald, P. J. J. Org. Chem. 1974, 39, 701–704.
cmÀ1
;
1H NMR (400 MHz, CDCl3): d = 5.55 (s, 4H,
J = 7.2 Hz, PhCH2O), 7.22–7.41 (m, 10H, Ar-H) ppm; 13
C
NMR (100 MHz, CDCl3): d = 74.5 (PhCH2O), 127.5,
128.5, 129.6, 131, 140.10, 142.20 (aromatic region), 158.5
(C@O) ppm; Mass (EIMS): m/e (%) = 243 (M+H+, 89%),
152 (42), 91(100); Anal. Calcd for C15H14O3: C, 74.36; H,
5.82. Found: C, 74.56; H, 5.61.