J. Org. Chem. 19912, 57, 389-391
389
3 H), 1.73-1.60 (m, 6 H), 1.35-1.01 (m, 14 H), 0.88 (t, 3 H, J = = 6.4 Hz), 3.66 (t, 2 H, J = 5.4 Hz), 2.02-1.93 (m, 4 H), 1.66 (8, 6.5Hz); I3C NMR (75MHz, CDC13) 6 136.4,127.8,40.7,33.3,32.7, 3 H), 1.561.27 (m, 10 H), 1.05 (8, 9 H), 0.88 (m, 3 H); I3C NMR 31.9,29.7,29.3,29.2, 29.1,26.3,26.2,26.0,22.7,14.1;MS (EI) mlz (75MHz, CDC13) 6 135.6,135.0,134.2,129.5,127.6,125.6,63.8, 208 (M+), 109,96,81,67,41.Anal. Calcd for Cl5HZ8:C, 86.46; 32.5,31.6,31.4,29.8,27.8,26.9,24.2,23.3,22.6,19.2,14.1; MS (E11 H, 13.54. Found C, 86.47;H, 13.71. m/z 365 (M - t-Bu+) 183,41.Anal. Calcd for C28H420Si:C, 79.56; H, 10.01. Found: C, 79.78;H, 10.22. Acknowledgment. We thank the National Science 1-[ (tert-Butyldiphenylsilyl)oxy]-5-methyl-5(E)-undecene Foundation (CHE-8815742 now numbered CHE-9096322) (12j): oil (0.83g, 62%); 99:l mixture of E / Z isomers; IR (film) for generous support of this program. Additionally, we 3071,2930,2858, 1590,1472,1112 cm-'; 'H NMR (300 MHz, CDC1,) 6 7.67-7.65 (m, 4 H),7.43-7.33 (m, 6 H), 5.10 (dt, 1 H, thank the National Institutes of Health for funding a J=1.2,7.2Hz),3.66(t,2H,J=6.1Hz),1.95(m,4H),1.661.28 400-MHz NMR spectrometer (RR 02314) and high-reso(m, 13 H), 1.05 (s, 9 H), 0.88 (t, 3 H, J = 6.7 Hz); 13CNMR (75 lution mass spectrometer (RR 03245) used in these studies MHz, CDC13)6 135.6,134.8,134.2,129.5,127.6,125.6,124.8,63.9, and G.D. Searle and Company for generous support and 39.3,32.1,31.6,29.6,27.9,26.9,24.1,22.6,19.2,15.8,14.1;MS (EI) for determining microanalyses. mlz 365 (M - t-Bu') 183,41.Anal. Calcd for C28H420Si:C, 79.56; Registry No. Sa,66-25-1; 8b, 124-13-0; SC, 2043-61-0; 8d, H, 10.01. Found: C, 79.91;H, 10.24. 100-52-7;9a, 125950-71-2; 9b, 115672-04-3; 9c,2043-61-0;9d, 6-Butyl-6(Z)-dodecene(12k): oil (0.24g, 65%); >95:95:
