3312
S. T. Kadam, S. S. Kim
PAPER
Naphthalen-2-ylmethanediyl Diacetate (Table 2, entry 5)
1H NMR (200 MHz, CDCl3): d = 2.15 (s, 6 H), 7.48–7.53 (m 3 H),
7.75 (s, 1 H), 7.89–7.90 (m, 3 H), 8.28 (m, 1 H).
13C NMR (100 MHz, CDCl3): d = 20.81, 89.54, 124.05, 124.87,
125.95, 125.99, 126.68, 128.69, 130.21, 130.53, 130.77, 133.88,
168.67.
2004, 627. (f) Chakraborti, A. K.; Gulhane, R. Tetrahedron
Lett. 2003, 44, 3521. (g) Tale, R. H.; Adude, R. N.
Tetrahedron Lett. 2006, 47, 7263. (h) Phukan, P.
Tetrahedron Lett. 2004, 45, 4785.
(4) (a) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H.
J. Org. Chem. 1996, 61, 4560. (b) Chauhan, K. K.; Frost,
C. G.; Love, I.; Waite, D. Synlett 1999, 1743.
HRMS (EI+): m/z [M + H]+ calcd for C15H14O4: 258.0892; found:
258.0895.
(c) Saravanan, P.; Singh, V. K. Tetrahedron Lett. 1999, 40,
2611. (d) Kamal, A.; Khan, M. N. A.; Reddy, K. S.;
Srikanth, Y. V. V.; Krishnaji, T. Tetrahedron Lett. 2007, 48,
3813. (e) Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Procopio,
A.; Nardi, M.; Bartoli, G.; Romeo, R. Tetrahedron Lett.
2003, 44, 5621. (f) Alleti, R.; Perambudura, M.; Samantha,
S.; Reddy, V. P. J. Mol Catal. A: Chem. 2005, 226, 57.
(5) (a) Nakae, Y.; Kusaki, I.; Sato, T. Synlett 2001, 1584.
(b) Kondasamy, J. K.; Chaand, D. K. J. Mol. Catal. A: Chem.
2006, 255, 275. (c) Bartoli, G.; Bosco, M.; Dalpozzo, R.;
Marcantoni, E.; Massaccesi, M.; Rinaldi, S.; Sambri, L.
Synlett 2003, 39.
(1E)-1-Phenylprop-1-ene-3,3-diyl Diacetate (Table 2, entry 6)
1H NMR (200 MHz, CDCl3): d = 2.08 (s, 6 H), 6.18 (d, J = 15.9 Hz,
1 H), 6.83 (d, J = 15.9 Hz 1 H), 7.27–7.39 (m, 5 H), 7.45 (s, 1 H).
13C NMR (100 MHz, CDCl3): d = 20.86, 89.70, 121.67, 126.99,
128.64, 128.80, 135.58, 168.65.
(4-Chlorophenyl)methanediyl Diacetate (Table 2, entry 8)
1H NMR (200 MHz, CDCl3): d = 2.11 (s, 6 H), 7.38 (d, J = 8 Hz,
2 H), 7.44 (d, J = 8 Hz, 2 H), 7.31 (s, 1 H).
(6) (a) Li, A.-X.; Li, T. S.; Ding, T. H. Chem. Commun. 1997,
15, 1389. (b) Reddy, T. S.; Narasimhulu, M.; Suryakiran,
N.; Mahesh, K. C.; Ashalatha, K.; Venkateswarlu, Y.
Tetrahedron Lett. 2006, 47, 6825. (c) Kumar, P.; Pandey,
R. K.; Bodas, M. S.; Dongare, M. K. Synlett 2001, 206.
(d) Zolfigol, M. A.; Khazaei, A.; Choghamarani, A. G.;
Rostai, A.; Hajjami, M. Catal. Commun. 2006, 7, 399.
(e) Kumareswaran, R.; Pachamuthu, K.; Vankar, Y. D.
Synlett 2000, 1652. (f) Grasa, G. A.; Kissling, R. M.; Nolan,
S. P. Org. Lett. 2002, 4, 3583.
13C NMR (100 MHz, CDCl3): d = 20.71, 88.91, 128.08, 128.75,
133.95, 135.61, 168.57.
(4-Nitrophenyl)methanediyl Diacetate (Table 2, entry 13)
1H NMR (200 MHz, CDCl3): d = 2.15 (s, 6 H), 7.26 (d, J = 8 Hz,
2 H), 7.34 (s, 1 H), 8.25 (d, J = 8 Hz, 2 H).
13C NMR (100 MHz, CDCl3): d = 20.70, 88.31, 123.81, 127.84,
141.88, 148.61, 168.51.
HRMS (EI+): m/z [M + H]+ calcd for C11H11NO6: 253.0586; found:
253.0586.
(7) Ferraz, H. M. C.; Silva, L. F. Jr.; de O. Vieira, T. Synthesis
1999, 2001.
(8) Ferraz, H. C. M.; Ribeiro, C. M. R. Quim. Nova 1990, 13, 88.
(9) McKillop, A.; Swann, B. P.; Taylor, E. C. J. Am. Chem. Soc.
1973, 95, 3340.
(3-Phenoxyphenyl)methanediyl Diacetate (Table 2, entry 15)
1H NMR (200 MHz, CDCl3): d = 2.20 (s, 6 H), 7.05 (d, J = 4 Hz,
2 H), 7.14–7.20 (m, 3 H), 7.33 (t, J = 8 Hz, 1 H), 7.38–7.41 (m,
3 H), 7.62 (s, 1 H).
13C NMR (100 MHz, CDCl3): d = 20.72, 89.09, 116.81, 119.04,
119.60, 121.24, 123.59, 129.77, 129.91, 137.29, 156.56, 157.49,
168.60.
(10) Ferraz, H. M. C.; Silva, L. F. Jr. Tetrahedron Lett. 1997, 38,
1899.
(11) Silva, L. F. Jr.; Craveiro, M. V.; Gambardella, M. T. P.
Synthesis 2007, 3851.
(12) Silva, L. F.; Quintiliano, S. A. P.; Craveiro, M. V.; Vieira,
F. Y. M.; Ferraz, H. M. C. Synthesis 2007, 355.
(13) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem.
Soc. 1994, 116, 186.
(14) Harmange, J.-C.; Figadere, B. Tetrahedron 1993, 4, 1711.
(15) Kiso, Y.; Fuji, N.; Yajima, H. Braz. J. Med. Biol. Res. 1994,
27, 2733.
Heptane-1,1-diyl Diacetate (Table 2, entry 16)
1H NMR (200 MHz, CDCl3): d = 0.88 (t, J = 6.2 Hz, 3 H), 1.31–
1.41 (m, 8 H), 1.85 (m, 2 H), 2.21 (s, 6 H), 6.29 (s, 1 H).
13C NMR (100 MHz, CDCl3): d = 13.92, 22.43, 23.27, 28.96, 31.61,
31.97, 90.53, 170.57.
(16) Kadam, S. T.; Kim, S. S. Synthesis 2008, 267.
(17) Trost, B. M.; Lee, C. J. Am. Chem. Soc. 2001, 123, 12191.
(18) Green, T. W.; Wuts, P. G. M. In Protective Groups in
Organic Synthesis, 3rd ed.; John Wiley & Sons: New York,
1999, 306.
Acknowledgment
The authors thank the Centre for Biological Modulators for finan-
cial support. BK21 has been provided from the Korea Research
Council.
(19) (a) Yadav, J. S.; Reddy, B. V. S.; Srinivas, C. Synth.
Commun. 2002, 32, 2169. (b) Sumida, N.; Nishioka, K.;
Sato, T. Synlett 2001, 1921. (c) Roy, S. C.; Banerjee, B.
Synlett 2002, 1677. (d) Deka, N.; Kalita, D. J.; Borah, R.;
Sarma, J. C. J. Org. Chem. 1997, 62, 1563. (e) Kochhar,
K. S.; Bal, B. S.; Deshpande, R. P.; Rajadhyaksha, S. N.;
Pinnick, H. W. J. Org. Chem. 1983, 48, 1765. (f) Kamble,
V. T.; Jamode, V. S.; Joshi, N. S.; Biradar, A. V.; Deshmukh,
R. Y. Tetrahedron Lett. 2006, 47, 5573. (g) Kavala, V.;
Patel, B. K. Eur. J. Org. Chem. 2005, 441. (h) Khan, A. T.;
Choudhury, L. H.; Ghosh, S. Eur. J. Org. Chem. 2005,
2782. (i) Romanelli, G. P.; Thomas, H. J.; Baronetti, G. T.;
Autino, J. C. Tetrahedron Lett. 2003, 44, 1301.
(20) (a) Lata Chandra, K.; Saravanan, P.; Singh, V. K. Synlett
2000, 359. (b) Orita, A.; Tanahashi, C.; Kakuda, A.; Otera,
J. Angew. Chem. Int. Ed. 2000, 39, 2877. (c) Aggarwal,
V. K.; Fonquerna, S.; Vennall, G. P. Synlett 1998, 849.
References
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Synthesis 2008, No. 20, 3307–3313 © Thieme Stuttgart · New York