References
- Yamamoto , Y. and Asao , N. 1993 . Chem. Rev. , 93 : 2207
- Roush , W.R. 1991 . Comprehensive Organic Synthesis Edited by: Trost , B.M. and Fleming , I. Vol. 2 , Oxford : Pergamon . Chapter 1
- Li , C.-J. 1996 . Tetrahedron , : 5643
- Ranu , B.C. 2000 . Eur. J. Org. Chem. , : 2347
- Li , C.J. and Chan , T.H. 1999 . Tetrahedron , 55 : 11149
- Cintas , P. 1995 . Synlett , : 1087
- Chan , T.-H. and Issac , M.B. 1996 . Pure Appl. Chem. , 68 : 919
- Marshall , J.A. 1997 . Chemtract.-Org. Chem. , 10 : 481
- Chauhan , K.K. and Frost , C.G. 2000 . J. Chem. Soc. Perkin Trans. 1 , : 3015
- Isaac , M.B. and Paquette , L.A. 1997 . J. Org. Chem. , 63 : 5333
- Li , C.-J. 1993 . Chem. Rev. , 93 : 2023
- Yi , X.-H. , Meng , Y. and Li , C.-J. 1997 . Tetrahedron Lett. , 38 : 4731
- Loh , T.-P. and Li , X.R. 1997 . Angew. Chem., Int. Ed. Engl. , 36 : 980
- Hoppe , H.A. , Lloyd-Jones , G.C. , Murray , M. , Peakman , T.M. and Walsh , K.E. 1998 . Angew.Chem. Int. Ed. , 37 : 1545
- Lloyd-Jones , G.C. and Russell , T. 1998 . Synlett , : 903
- Haldar , M. , Kar , G.K. and Ray , J.K. 1997 . Synlett , 9 : 1057 and the references cited therein
- Ghosh , M. , Mukherjee , R. , Chatterjee , B.G. and Ray , J.K. 1981 . Ind. J. Chem. Sec. B , 20 : 243
- Ray , J.K. , Sharma , S. and Chatterjee , B.G. 1979 . Synth. Commun. , 9 : 727
- Haldar , M. , Kar , G.K. , Gupta , S. and Ray , J.K. 2000 . Tetrahedron , 56 : 909
- Ray , J.K. , Sharma , S. and Chatterjee , B.G. 1980 . Synthesis , 4 : 326
- Ramesh , D. , Chatterjee , B.G. and Ray , J.K. 1986 . Ind. J. Chem. , : 984
- Ray , J.K. , Kar , G.K. and Chatterjee , B.G. 1984 . Tetrahedron , 40 : 2959
- Ray , J.K. , Gupta , S. , Pan , D. and Kar , G.K. 2001 . Tetrahedron , 57 : 7213
- Ray , J.K. Unpublished results
- Chakraborty , A. and Ray , J.K. 1995 . Synth. Commun. , 25 : 1869
- Ray , J.K. Unpublished results
- Sami , M.I. , Kar , G.K. and Ray , J.K. 1992 . Tetrahedron , 48 : 5199
- Typical experimental procedure: A mixture of β-chlorovinylaldehyde (1 mmol), allyl bromide (3 mmol), indium metal (Sisco Research Laboratory India) (2 mmol), sodium iodide (3 mmol) in dimethyl formamide (4–5 mL) was stirred at 25°C until completion of the reaction (checked by TLC). The reaction mixture was quenched with a few drops of 1N HCl, diluted with water and extracted with diethyl ether. After usual work up, the crude product obtained was purified by column chromatography (silica gel)
- All compounds gave satisfactory elemental and spectroscopic data
- Data of the product 15c 1H NMR (CDCl3) δ: 1.9 (brs, 1H), 2.26–2.53 (m, 4H), 2.53–2.74 (m, 2H), 5.04–5.20 (m, 3H), 5.71–5.92 (m, 1H), 6.96 (d, 1H, J = 8.0 Hz), 7.28 (dd, 1H, J = 2.0 & 8.0 Hz), 7.71 (d, 1H, J = 2.0 Hz) ppm; 13C NMR 23.09, 27.12, 39.26, 70.32, 118.39, 120.23, 124.34, 127.42, 128.46, 130.64, 133.58, 134.67, 135.01, 139.27; DEPT 135: 23.09, 27.13, 39.27, 70.31, 118.41, 127.42, 128.48, 130.64, 133.57. DEPT 90: 70.31, 127.41, 128.48, 130.65, 133.57. CHN calcd: C (53.59), H (4.47). Observed: C (53.35), H (4.27). Data of the product 201H NMR (CDCl3) δ: 1.85 (br, 1H), 2.37–2.50 (m, 4H), 4.81 (m, 2H), 5.16–5.24 (m, 4H), 5.87–5.95 (m, 2H), 6.13 (d, 2H, J = 7.6 Hz), 7.00 (dd, 4H, J = 2.2 & 6.8 Hz), 7.55 (dd, 4H, J = 2.2 & 6.8 Hz) ppm. 13C NMR 40.81, 68.88, 109.90, 118.58, 118.73, 128.13, 128.69, 133.51. CHN calcd: C (66.82), H (5.57). Observed: C (66.57), H (5.31)
- Yamaguchi , R. 1982 . Synth. Commun. , 12 : 1027