6,6-DIMETHYLBICYCLO[3.1.0]HEXANE DERIVATIVES 113 Table II Spectral Data and Elemental Analysis of Products Compound 1H-NMR IR (CC14, 8) (cm -1) Elem. Anal. %C, %H, %N 8 9 10 11a,b 12 1.24 (s, 6H, (CH3)2C) 1.38 (s, 6H, -C(CH3)2OH) 2.34 (s, 1H, -OH) 1.25 (s, 6H, (CH3)2C) 1.32 (s, 3H, CH3-C-OH) 5.20 (q, 2H, J=7Hz, -CH2CH3) 1.30 (s, 6H, (CH3)2C) 1.38 (s, 3H, CH3-C-OH) 1.81 (s, 1H, -OH) 2.41 (d, 2H, J=7Hz, -CH 2-CH=CH2) 3.55-3.95 (m, 1H, -CH(OH)-) 5.21-5.43 (m, 2H, H2C=CH-) 5.84-6.28 (m, 1H, H2C=CH-) 1.24 (s, 6H, (CH3)2C) 1.41 (d, 3H, J=6Hz, CH•CH-) 2.24 (s, 3H, CH3CO-) 4.88 (qt, 1 H, J = 6Hz, - HCOAc) a: 1.27 and 1.28 (2s, 6H, (CH3)2C) 1.54 (t, 3H, J=7Hz, CH3CH20-) 2.40 (s, 3H, =CCH_•), 2.93 (qt, 1H, J=8Hz, H at C-3) 4.37 (q, 2H, J=7Hz, CH3CH2-) 5.85 (s, 1H, =CH-) b: 1.26 and 1.36 (2s, 6H, (CH3)2C) 1.54 (t, 3H, J=7Hz, CH3CH2-) 2.13 (s, 3H, =CCH0 4.37 (q, 2H, J=7Hz, CH3CH2-) 4.62 (qt, 1H, J=8Hz, H at C-3) 5.75 (s, 1H, =CH-) 1.23 (s, 6H, (CH3)2C) 1.40 (d, 3H, J=6Hz, -CHCH3) 1.54 (t, 3H, J=7Hz, CH3CH2-) 4.36 (q, 2H, J=7Hz, CH3CH2-) 3380 (vs,vb), 3000 (s), 2965 and 2930 (vs), 2865 (m), 1465 and 1460 (m), 1365 (s), 1125 (s) 3415 (vs,vb), 3000 (s), 2970 and 2940 (vs), 2865 (s), 1455 (s), 1370 (s), 1120 (s) 3440 (vs,vb), 3085 (m), 3020 (m), 2985 (w), 2930 (vs), 2865 (s), 1640 (m), 1115 (s) 990 (m), 905 (s) 3005 (m), 2975 (m), 2975 (s), 2940 (s), 1725 (s), 1455 (s) 1365 (m), 1235 (s) a: and b: 301.0 (m), 2980 (m), 2940 (s), 2865 (m), 1705 (vs), 1640 (s) 3005 (m), 2955 (s), 2920 (vs), 2865 (s), 1735 (vs), 1155 (s) CllH2o ¸ (168.28) Calcd: 78.51, 11.98 Found: 78.38, 12.02 C12H220 (182.31) Calcd: 79.06, 12.16 Found: 78.89, 12.19 C13H220 (194.30) Calcd: 80.35, 11.41 Found: 80.26, 11.34 C• •H2oO2(184.28) Calcd: 73.43, 10.27 Found: 73.27, 10.41 C•4H2202(222.23) Calcd: 75.63, 9.97 Found: 75.41, 10.07 C•4H2402(224.34) Calcd: 77.95, 10.78 Found: 77.59, 10.82

114 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS Table II (continued) Compound •H-NMR IR (CC14, 8) (cm -•) Elem. Anal. %C, %H, %N 14 15a 16a,b 17 18 2O 21a,b 1.22 (s, 6H, (CH3)2C) 2.15 (s, 1H, -OH) 3.75-4.02 (m, 1H, -CHOH-), 5.22-5.46 (m, 2H, -CH=CH2), 5.86-6.30 (m, 1H, -CH2-CH-CH2) 1.22 (s, 6H, (CH3)2C) 2.43 (s, 3H, CH3CO-) 6.24 (d, 1H, J=16Hz, -CH=CH-CO-) 6.93 (dr, 1H, -C(Hc)2CHb=CHa -, Jab = 16Hz, Jbc=8Hz) 1.27 and 1.37 (2s, 6H, (CH•)2C) 2.32 (s, 3H, =CCH3) 2.91 (qt, 1H, J=8Hz, H at C-3, isomer E) 3.50-3.70 (m, 1H, H at C-3, isomer Z) 5.18 (s, 1H, =CH-, isomer Z) 5.33 (s, 1H, =CH-, isomer E) 1.30 (s, 6H, (CH3)2C) 1.41 (d, 3H, J=6Hz, -CHCH 3) 1.12 and 1.28 (2s, 6H, (CH3)2C) 2.03 (s, 3H, =CCH3) 3.20 (s, 2H, -CH2CN) 1.22 (s, 6H, (CH3)2C) 1.99 (s, 1H, -OH) 3.47-3 70 (m, 1H, -CH(OH)-) 5.21-5.43 (m, 2H, H2C=CH) 5.84-6.28 (m, 1H, H2C=CH-) 1.26 and 1.35 (2s, 6H, (CH•)2C) 2.60-3.08 (m, 1H, H at C-3, isomer E) 3.13-3.60 (m, 1H, H at C-3, isomer Z) 5.35 (s, 1H, -CH=CHCN, isomer Z) 5.41 (s, 1H, -CH=CHCN, isomer E) 6.58 (dd, 1H, -CHcCHb=CHa-, Jab= 10Hz, Jbc=9Hz, isomer Z) 6.79 (dd, 1H, CHcCHb=CHa-, Jab= 16Hz, Jbc=9Hz, isomer E). 3355 (vs,vb), 3080 (w), 3005 (m), 2925 (vs), 2865 (s), 1640 (w), 1445 (m), 1365 (w). 3005 (s), 2925 and 2865 (vs), 1690 and 1665 (vs), 1620 (s), 1445 and 1425 (s), 1370 and 1355 (s) 3010 (m), 2940 (s), 1865 (m), 2220 (m), 1635 (s), 1450 and 1375 (m) 3020 (vs), 2950 (vs), 2870 (vs), 2220 (m), 1460 (s), 1375 (s) 3030 (s), 2995 (vs), 2265 (m), 1440 (s), 1420 (s), 1375 (s) 3365 (vs,vb), 3075 (m), 3005 (s), 2980 (w), 2935 (vs), 2860 (s), 1640 (m), 1005 (s), 990 (m), 905 (s) 3020 (m), 2940 (s), 2865 (m), 2215 (s), 1620 (m), 1450 and 1375 (m), 975 (s) 715 (m) C15H260 (222.37) Calcd: 81.02, 11.79 Found: 81.10, 11.71 C15H240 (220.35) Calcd: 81.76, 10.98 Found: 81.51 11.10 C•2H•7N (175.27) Calcd: 82.23, 9.78, 7.99. Found: 82.40, 9.80, 8.10 C•2H•9N (177.29) Calcd: 81.30, 10.80, 7.90 Found: 81.52, 10.83, 7.95 C12H2o ¸ (180.29) Calcd: 79.94, 11.18 Found: 79.52, 11.28 CnH•5N (161.25) Calcd: 81.94, 9.38, 8.69. Found: 82.03, 9.30, 8.77