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A. Kamal et al. / Tetrahedron Letters 48 (2007) 3813–3818
12. (a) Olah, G. A.; Farooq, O.; Farnia, S. M. F.; Olah, J. A.
J. Am. Chem. Soc. 1988, 110, 2560; (b) Williams, D. B. G.;
Lawton, M. Org. Biomol. Chem. 2005, 3, 3269; (c)
Williams, D. B. G.; Lawton, M. Tetrahedron Lett. 2006,
47, 6557; (d) Terblans, Y. M.; Huyser, J.; Huyser, M.;
Green, M. J.; Yound, D. A.; Sibiya, M. S. Can J. Chem./
Rev. Can. Chim. 2005, 83, 854; (e) Firouzabadi, H.;
Iranpoor, N.; Kohmareh, G. Synth. Commun. 2003, 33,
167; (f) Firouzabadi, H.; Iranpoor, N.; Sobhani, S.;
Ghassamipour, S. Synthesis 2005, 4, 595.
13. Selected spectral data for the acetylated products: Tetra-
hydro-2-furanylmethyl acetate (entry 18), semi solid, 1H
NMR (CDCl3, Me4Si, 300 MHz) d (ppm): 4.02–4.14
(m, 2H), 3.92–4.00 (m, 1H), 3.86 (q, J = 6.80 Hz, 1H),
3.77 (q, J = 7.55 Hz, 1H), 2.08 (s, 3H, COCH3), 1.84–2.07
(m, 3H), 1.54–1.68 (m, 1H). IR (KBr) (m/cmꢀ1): 2955,
2874, 1742 (OC@O), 1370, 1237 (CO–O), 1040. EI-MS:
M+ 144. Anal. Calcd for C7H12O3: C, 58.32; H, 8.39.
Found: C, 58.39; H, 8.36. 3-(Acetyloxy)-2,2-di[(acetyl-
oxy)methyl]propyl acetate (entry 19), mp 78–80 ꢁC, 1H
NMR (CDCl3, 300 MHz) 2.08 (s, 12H, 4COCH3), 4.10 (s,
8H). IR (KBr) (m/cmꢀ1): 2975, 2906, 1738 (OC@O), 1236
(CO–O), 1041. LC-MS: 327 [M+Na]+. Anal. Calcd for
C13H20O8: C, 51.38; H, 6.62. Found: C, 51.45; H, 6.58. 2-
Oxo-2H-7-chromenyl acetate (entry 20), mp 143–145 ꢁC,
1H NMR (CDCl3, Me4Si, 200 MHz) d (ppm): 7.68
(d, J = 9.37 Hz, 1H), 7.48 (d, J = 8.59 Hz, 1H), 7.12 (d,
J = 2.34 Hz, 1H), 7.04 (dd, J = 8.59, 2.34 Hz, 1H), 7.38 (d,
J = 9.37 Hz, 1H), 2.35 (s, 3H, COCH3). IR (KBr)
(m/cmꢀ1): 1742 (OC@O), 1621, 1203, 1186 (CO–O), 848.
EI-MS: M+ 204. Anal. Calcd for C11H8O4: C, 64.71; H,
3.95. Found: C, 64.75; H, 3.94. 9-Oxo-9H-2-fluorenyl
acetate (entry 21), mp 158–159 ꢁC, yellow crystalline solid.
1H NMR (CDCl3, Me4Si, 200 MHz) d (ppm): 7.62 (d,
J = 7.81 Hz, 1H), 7.48 (d, J = 7.81 Hz, 2H), 7.44 (s, 1H),
7.35 (d, J = 2.34 Hz, 1H), 7.24–7.32 (m, 1H), 7.15 (dd,
J = 8.59, 2.34 Hz, 1H), 2.31 (s, 3H, COCH3). 13C NMR
(CDCl3, Me4Si, 75 MHz) d (ppm): 192.5, 169.0, 151.4,
143.8, 141.6, 135.5, 134.8, 134.3, 128.8, 127.3, 124.4, 121.0,
120.2, 118.0, 20.9. IR (KBr) (m/cmꢀ1): 3060, 1762
(OC@O), 1716 (C@O), 1600, 1455, 1196, 1126 (CO–O),
1013, 736. EI-MS: M+ 238; M+-42 (196, base peak). Anal.
Calcd for C15H10O3: C, 75.62; H, 4.23. Found: C, 75.69;
H, 4.21. Dibenzo[b,d]furan-3-yl acetate (entry 22), mp
110–112 ꢁC, 1H NMR (CDCl3, Me4Si, 300 MHz) d (ppm):
7.86 (d, J = 7.55 Hz, 1H), 7.63 (d, J = 2.26 Hz, 1H), 7.50–
7.55 (m, 2H), 7.42 (dt, J = 8.31, 1.51 Hz, 1H), 7.24–7.34
(m, 1H), 7.12 (dd, J = 9.06, 2.26 Hz, 1H), 2.33 (s, 3H,
COCH3). IR (KBr) (m/cmꢀ1): 1755 (OC@O), 1446, 1222,
1158 (OC–O), 1012, 745. EI-MS: M+ 226. Anal. Calcd for
C14H10O3: C, 74.33; H, 4.46. Found: C, 74.39; H, 4.43.
14. (R)-3-Acetyloxy-3-phenylpropanenitrile (entry 24):
A
25
white solid; mp 120–121 ꢁC {lit.15a mp 121–124 ꢁC}; ½aꢁD
30
+70 (c 1.0, CHCl3) {lit.15a ½aꢁD +71.9 (c 1.0, CHCl3)}.
25
Menthyl acetate (entry 25): ½aꢁD +79 (c 1.0, CHCl3) {lit.15b
[a]D +80}. 1,2,3,4,5,6-Hexa-O-acetyl-D-mannitol (entry
28): A white crystalline solid; mp 121–122 ꢁC {lit.15c mp
25
30
123–124 ꢁC} ½aꢁD +26 (c 1.0, CHCl3) {lit.15c ½aꢁD +27 (c
1.0, CHCl3)}.
15. (a) Kamal, A.; Khanna, G. B. R.; Ramu, R. Tetrahedron:
Asymmetry 2002, 13, 2039; (b) Kantam, M. L.; Aziz, K.;
Likhar, P. R. Catal. Commun. 2006, 7, 484; (c) Dasgupta,
F.; Singh, P. P.; Srivastava, H. C. Carbohydr. Res. 1980,
80, 346.