ORDER
REPRINTS
2
602
RAMESH ET AL.
,2-Diacetoxy-cyclohexane 1a: Bp 116–118 C, IR (neat) v(max): 1735,
6
ꢀ
1
–
1 1
1
730, 1239, and 1095 cm . H NMR (200 MHz, CDCl ): d 4.75 (d, 2H,
3
þ
J ¼ 16 Hz), 2.02 (br s, 6H), 1.23–1.75 (m, 8H). EIMS: m/z (%) 200 [M ]
3), 142 (87), 141 (5), 99 (45), 81 (80), 70 (8), and 43 (100). Anal. Calcd
for C H O : C, 59.98; H, 8.05. Found: C, 59.86; H, 8.08.
(
1
0
16
4
7
ꢀ
1
,2-Diacetoxy-1-phenyl-ethane 2a: Bp: 119–120 C, IR (neat) v(max):
–
1 1
3
010, 1738, 1730, and 1360 cm . H NMR (200 MHz, CDCl ): d 7.3 (br
3
s, 5H), 6.0(dd, 1H, J ¼ 7.2, 5.1 Hz), 4.3 (2H, m), 2.08 (br s, 3H), 2.11 (s,
þ
3
1
H). EIMS: m/z (%) 222 [M ] (3), 195 (4), 164 (31), 150(11), 122 (15),
07 (35), 105 (100), 91 (93), 77 (46), 57 (9), and 43 (93). Anal. Calcd for
7
b
C H O : C, 68.85; H, 6.35. Found: C, 64.82; H, 6.41.
1
2
14
4
8
,2-Diacetoxy-hexane 3a: Bp 107–108 C, IR (neat) v(max): 2940, 1736,
ꢀ
1
–
1 1
1
3
732, 1262, and 1130cm . H NMR (200 MHz, CDCl ): d 5.01 (m, 1H),
3
.96 (dd, 1H, J ¼ 8.1, 6.2 Hz), 4.2 (dd, 1H, J ¼ 5.1, 3.2 Hz), 2.05 (d, 6H,
þ
J ¼ 16 Hz), 1.6 (br s, 6H), 0.89 (t, 3H). EIMS: m/z (%) 202 [M ] (2),
1
71 (51), 158 (4), 142 (3), 129 (8), 127 (10), 111 (25), 97 (12), 69 (75), 57
(
Found: C, 59.28; H, 8.95.
18), 55 (41), and 43 (100). Anal. Calcd for C H O : C, 59.39; H, 8.97.
1
0
18
4
9
,2-Diacetoxy-3-chloro-propane 4a: Bp 95–96 C, IR (neat) v(max):
ꢀ
1
736, 1730, 1240, 1080, and 720 cm . H NMR (200 MHz, CDCl3):
–
1
1
1
d 5.18 (m, 1H), 4.19 (dd, 1H, J ¼ 10, 8.1 Hz), 4.36 (dd, 1H, J ¼ 8.2, 4.5 Hz),
þ
3
.65 (t, 2H), 2.08 (s, 3H), 2.12 (s, 3H). EIMS: m/z (%) 135 [M -AcOH]
(
C H ClO : C, 43.20; H, 5.70; Cl, 18.22. Found: C, 43.41; H, 5.92; Cl,
10), 119 (22), 76 (14), 60 (6), 57 (70), and 43 (97). Anal. Calcd for
9
a
7
11
4
1
8.25.
1
,2,3-Triacetoxy-propane 5a: Bp 258–259 C, IR (neat) v(max): 1746,
0
ꢀ
1
734, 1728, 1330, 1242, and 1165 cm . H NMR (200 MHz, CDCl3):
–
1
1
1
d 5.2 (m, 1H), 4.12 (dd, 2H, J ¼ 10, 6.1 Hz), 4.4 (dd, 2H, J ¼ 6.1, 4.2 Hz),
2
1
6
.1 (br s, 9H). EIMS: m/z (%) 218 (28), 176 (27), 148 (8), 129 (12), 120(9),
02 (20), 85 (47), 72 (27), and 60 (24). Anal. Calcd for C H O : C, 49.54; H,
9
14
6
.47. Found: C, 49.47; H, 6.50.
-(4-Methylphenoxyl)-1,2-diacetoxy-propane 6a: Bp 163–165 C, IR
1
1
ꢀ
3
neat) v(max): 3030, 1742, 1733, and 1280 cm . H NMR (200 MHz,
–
1
1
(
CDCl ): d 7.05 (d, 2H, J ¼ 12 Hz), 7.78 (d, 2H, J ¼ 10Hz), 5.31 (m, 1H),
3
4.42 (dd, 1H, J ¼ 7.5, 5.1 Hz), 4.23 (dd, 1H, J ¼ 10, 7.5 Hz), 4.18 (t, 2H),
2.3 (s, 3H), 2.1 (s, 3H), 2.08 (s, 3H). EIMS: m/z (%) 266 (3), 154 (8), 159 (62),
147 (8), 121 (15), 108 (35), 91 (15), 57 (8), and 43 (100). Anal. Calcd for
C H O : C, 63.15; H, 6.81. Found: C, 63.10; H, 6.84.
1
4
18
5
1
,15-Diacetoxyafricanane 7a: IR (neat) v(max): 1735, 1740, 1260, and
2
9
–
1 1
1
1
0
095 cm , H NMR (200 MHz, CDCl ): d 4.62 (d, 1H, J ¼ 13 Hz), 4.12 (d,
3
H, J ¼ 13 Hz), 2.04 (s, 3H), 2.02 (s, 3H), 1.5–1.9 (m, 7H), 0.95 (s, 3H),
.90 (s, 3H), 0.88 (s, 3H), 0.52 (m, 2H), 0.18 (m, 1H). EIMS: m/z (%) 262