1214
LETTERS
SYNLETT
temperature was allowed to rise to room temperature. After stirring for
18 hours, saturated NH4Cl solution (15 mL) and Et2O(15 mL) were
added and the mixture was stirred for 20 minutes. The organic layer was
separated, dried over anhydrous MgSO4 and concentrated. The product
was isolated from the crude reaction mixture by chromatography on
silica gel ( petroleum/dichloromethane or diethyl ether).
J=7.35Hz); EI-MS m/z 132(M+, 99%), 117(100), 104(33), 103(35),
91(98), 77(76)
3g Colorless liquid, IR υmax(neat)/cm-1 3065, 2966, 2930, 2874, 1647,
1591, 1566, 1469, 1437, 964, 746, 690; 1H NMR δH(80MHz; CDCl3)
7.60-7.13(m, 4H), 6.88-6.05(m, 2H), 2.48-2.14(m, 2H), 1.11(t, 3H,
J=7.43Hz); 13C NMR δc(100MHz; CDCl3) 135.9, 135.5, 132.5, 129.5,
127.8, 126.7, 126.5, 125.1, 26.3, 13.5; EI-MS m/z 166(M+, 99%),
151(100), 138(12), 131(97), 116(99), 91(73), 77(21)
3a Colorless liquid, IR υmax(neat)/cm-1 3057, 3026, 2959, 2928, 2856,
1
1655, 1599, 1493, 1462, 962, 740, 692; H NMR δH(80MHz; CDCl3)
7.35-7.19 (m, 5H), 6.51-6.19(m, 2H), 2.16(q, 2H, J=5.5Hz), 1.58-
1.21(m, 6H), 0.90(t, 3H); 13C NMR δc(100Mhz; CDCl3) 137.9, 131.2,
129.9, 1128.4(2C), 126.7, 125.9(2C), 33.0, 31.2, 29.1, 22.6, 14.1; EI-
MS m/z 174(M+, 58%), 117(100), 104(99), 103(98), 91(78), 77(14)
References and notes
(1) (a) Knochel, P.; Singer, R.D. Chem. Rev. 1993, 93, 2117; (b)
Rieke, R.D.; Hason, M.V. Tetrahedron 1997, 53, 1925
3b Colorless liquid, IR υmax(neat)/cm-1 3080, 3026, 2955, 2933, 2864,
1651, 1597, 1577, 1493, 1446, 966, 742, 694, 650; 1H NMR
δH(80MHz; CDCl3) 7.36-7.04(m, 5H), 6.53-6.00(m, 2H), 3.54(t, 2H,
J=6.2Hz), 2.37(q, 2H, J=6.8Hz), 2.36-1.49(m, 4H); EI-MS m/z 194(M+,
77%), 117(100), 104(68), 103(31), 91(94), 77(17)
(2) Oppolzer, W.; Radinov, R.N. J. Am. Chem. Soc. 1993, 115, 1593
(3) (a) Sato, T.; Soai, K.; Suzuki, K.; Mukaiyama, T. Chem. Lett.,
1978, 601; (b) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H;
Suzuki, K. J. Am. Chem., Soc. 1979, 101, 1455
(4) Nakamura, E.; Aoki, S.; Sekiya, K.; Oshino, H.; Kuwajima, I. J.
Am. Chem. Soc. 1987, 109, 8056
3c Colorless liquid, IR υmax(neat)/cm-1 3060, 3028, 2965, 2928, 2872,
1648, 1596, 1567, 1468, 1437, 964, 745, 691; 1H NMR δH(80MHz;
CDCl3) 7.56-7.13(m, 4H), 6.86-6.01(m, 2H), 2.03-3.13(q, 2H,
J=6.4Hz), 1.66-1.27(m, 6H), 0.91(t, 3H, J=5.5Hz); EI-MS m/z 208(M+,
99%), 173(19), 165(27), 151(100), 138(98), 125(97), 89(95), 77(8)
(5) (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833; (b) Noyori, R.;
Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991. 30. 49
(6) Knochel, P.; Yeh, M.C.P.; Berk, S.C.; Talbert, J. J. Org. Chem.
1988, 53, 2390
3d Colorless liquid, IR υmax(neat)/cm-1 3061, 3038, 2937, 2864, 2841,
1649, 1591, 1556, 1469, 1441, 966, 750, 694, 651; 1H NMR
δH(80MHz; CDCl3) 7.54-7.14(m, 4H), 6.68-6.05(m, 2H), 3.56(t, 2H,
J=6.18Hz), 2.42-2.16(q, 2H, J=7.02Hz), 1.93-1.62(m, 4H); EI-MS m/z
230(M+, 40%), 195(5), 151(100), 150(99), 138(98), 125(71), 115(97),
77(10)
(7) (a) Micouin, L.; Oestreich, M.; Knochel, P. Angew. Chem., Int.
Ed. Engl. 1997, 36, 245; (b) Jackson, R.F.W.; Turner, D.; Block,
M. H. J. Chem. Soc., Perkin Trans.1 1997, 865; (c) Rossi, R.;
Bellina, F.; Ciucci, D. J. Organometal. Chem. 1997, 542, 113; (d)
Jou, D.-C.; Hsiao, T.-Y.; Wu, M.-Y.; Kong, K.-C.; Cheng, C.-H.
Tetrahedron 1998, 54, 1041
3e Colorless liquid, IR υmax(neat)/cm-1 3030, 3001, 2937, 2928, 2856,
2835, 1610, 1574, 1512, 1464, 1441, 1248, 964, 798; 1H NMR
δH(80MHz; CDCl3) 7.32-6.84(m, 4H), 6.45-5.80(m, 2H), 3.78(s, 3H),
2.21-2.13(m, 2H), 1.50-1.98(m, 6H), 0.90(t, 3H); EI-MS m/z 204(M+,
99%), 147(100), 134(66), 121(65), 91(95), 90(53), 77(11)
(8) Hu, Y.; Yu, J.; Yang, S.; Wang, J; Yin, Y. Synth. Commun. 1998,
28, 2793
(9) (a) Bunnett, J.F.; Zahler, R.E. Chem. Rev. 1951, 49, 273; (b)
Bunnett, J.F.; Garbisch, Jr, E. W.; Pruitt, K.M. J. Am. Chem. Soc.
1957, 79, 385; (c) Berk, J.R. J. Org. Chem. 1978, 43, 2048; (d)
Guo, H.Y. Huaxueu Yongbao 1983, 5, 38
3f Colorless liquid, IR υmax(neat)/cm-1 3028, 2967, 2930, 2874, 1651,
1599, 1493, 1452, 964, 742, 692; 1H NMR δH(80MHz; CDCl3) 7.41-
7.10(m, 5H), 6.53-6.24(m, 2H), 2.40-2.07(m, 2H), 1.09(t, 3H,
(10) Seebach, D.; Schäfer, H.; Schmidt, B.; Schreiber, M. Angew.
Chem., Int. Ed. Engl. 1992, 31, 1587