References
- LaCombe , E. M. and Stewart , B. 1961 . J. Am. Chem. Soc. , 83 : 3457 For early reports of this reaction see
- Hendrickson , J. B. and Bergeron , R. 1973 . Tetrahedron Lett. , : 3609
- Unpublished results of R. D. Little, L. W. Linder, Jr., S. O. Myong and S. C. Seike
- Ho , T.-L. 1974 . Synthetic Communications , 4 : 265
- Ho , T.-L. 1977 . Synthetic Communications , 7 : 351
- Biellmann , J-Francois and Schirlin , D. 1978 . Synthetic Communications , 8 : 409
- Tsuji , J. and Yasuda , H. 1978 . Synthetic Communications , 8 : 103 and references cited in (a)-(d) above
- Krishnamurthy , S. and Brown , H. C. 1977 . J. Org. Chem. , 42 : 1197
- Stork , G. , Grieco , P. A. and Gregson , M. 1974 . Organic Syntheses , 54 : 68
- Eaton , P. E. , Carlson , G. R. and Lee , J. T. 1973 . J. Org. Chem. , 38 : 4071
- Trost , B. M. and Bogdanowicz , M. J. 1973 . J. Amer. Chem. Soc. , 95 : 5321 Spectral data for 3 ir (neat) 3350, 2900, 1650, 1000, 900 cm−1; 1H nmr (CDCI3) δ 5.0 (m, 1 H, vinyl), 4.8 (m, 1 H, vinyl), 4.03 (br s, 2 H, CH2OH), 2.76 (br s, variable position, 1 H, OH) 1.1–2.2 (m, 10 H, CH2), 0.9 (br ill defined t, 3 H, CH3); for 5: ir (film) 3060, 2950, 2910, 2840, 1730, 1630, 910 cm−1; 1H nmr (CDCl3) δ 4.91 (br s, 2 H, vinyl), 3.74 (s, 3 H, -CO2CH3), 3.28 (2 H, CH2=CRCH2SR'), 3.15 (s, 2 H, RSCH2CO2Me), 1.2–2.4 (m, 10 H, CH2), 0.91 (t, 3 H, CH3); for 6: ir (film) 2940, 2910, 2840, 1725, 1640, 1320, 1110, 920 cm−1; 1H nmr (CDCl3) 5.21 (narrow m, 2 H, vinyl), two absorptions centered at 4.02 and 3.95 (4 H, CH2's α to SO2), 2.8 (s, 3 H, CH3), 2.05–2.4 (m, 2 H, allylic CH2), multiplet centered at 1.3 (8 H, CH2), 0.9 (ill defined t, 3H, J = 5 Hz, CH3); for 7; ir (neat) 2900, 1725, 910 cm−1; 1H nmr (CDCl3) δ 4.78 (m, 2 H, vinyl), 3.7 (s, 3 H, CO2CH3); 1.1–2.5 (m, 14 H, -CH2-), 0.9 (ill defined triplet, 3 H, CH3); for 9: see
- SW, TS, SCS, LWL, and LP all were NSF-URP program participants at UCSB