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M. Ishizaki et al. / Journal of Fluorine Chemistry 111 .2001) 81±90
4.27. 4-.2,2,2-Trifluoro-1-hydroxyethyl)-2-tosyl-2,3,3a,4-
tetrahydro-1H-cyclopenta[c]pyrrol-5-one .22)
4.31. 6-.Pentafluorophenyl)-2-tosyl-2,3,3a,4-tetrahydro-
1H-cyclopenta[c]pyrrol-5-one .26)
Obtained as an inseparable mixture of diastereomers; mp
118±1278C; 1H NMR d 7.72, 7.36 0each 2H, d, J 8:3 Hz),
6.01 01H, s), 4.51±4.60 01H, m), 4.32, 4.07 0each 1H, d,
J 16:8 Hz), 3.97 01H, t, J 9:3 Hz), 3.45±3.55 01H, m),
2.68±2.75 01H, m), 2.42 03H, s), 2.33 01H, dd, J 1:3,
3 Hz); 13C NMR d 205.5, 180.0, 144.2, 133.3, 130.0, 127.4,
124.4, 122.9, 66.1, 52.5, 51.6, 47.8, 43.6, 21.5; IR 3432,
Mp 64±658C; 1H NMR d 7.71, 7.34 0each 2H, d,
J 8:1 Hz), 4.36, 4.02 0each 1H, d, J 17:2 Hz), 4.12
01H, t, J 8:6 Hz), 3.22±3.40 01H, m), 2.68±2.89 02H, m),
2.43 03H, s), 2.30 01H, dd, J 3:3, 18.2 Hz); 13C NMR d
201.9, 178.3, 146.1, 144.4, 143.8, 139.7, 135.4, 133.5,
130.1, 127.4, 125.0, 52.3, 47.8, 43.1, 39.9, 21.6; IR 1726,
1686, 1652, 1597 cmÀ1; MS m/z 443 0M ); high-resolution
1712, 1649, 1597 cmÀ1; MS m/z 375 0M ); high-resolution
mass m/z calcd for C20H14F5NO3S 0M ) 443.0615, found:
443.0623.
mass m/z calcd for C16H16F3NO4S 0M ) 375.0752, found:
375.0742.
4.32. Dimethyl 6-.4-trifluoromethylphenyl)-5-oxo-
3,3a,4,5-tetrahydro-1H-pentalene-2,2-dicarboxylate .28)
4.28. 4-.2,2,2-Trifluoro-1-hydroxy-1-methylethyl)-2-tosyl-
2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one .23)
Oil; 1H NMR d 7.69, 7.65 0each 2H, d, J 8:9 Hz), 3.84,
3.73 0each 3H, s), 3.69, 3.31 0each 1H, d, J 19:5 Hz),
3.08±3.25 01H, m), 2.81±2.93 02H, m), 2.33 01H, dd,
J 3:5, 18 Hz), 1.73 01H, t, J 12:6 Hz); 13C NMR d
206.3, 180.6, 171.8, 170.9, 134.3, 129.9, 128.6, 125.3, 61.0,
53.3, 53.1, 43.1, 42.4, 38.6, 35.9; IR 2957, 1735, 1698,
Obtained as an inseparable mixture of diastereomers; mp
104±1128C; 1H NMR d 7.73, 7.36 0each 2H, d, J 8:3 Hz),
6.02 01H, s), 4.36, 4.07 0each 1H, d, J 17:2 Hz), 3.20±3.35
02H, m), 2.63±2.76 01H, m), 2.44 03H, s), 2.27 01H, d,
J 2:3 Hz), 1.53 03H, s); 13C NMR d 206.3, 178.2, 144.4,
133.3, 130.0, 127.5, 127.4, 125.1, 74.0, 56.0, 52.2, 47.6,
46.0, 45.4, 21.6; IR 3504, 1692, 1653, 1597 cmÀ1; MS m/z
1636 cmÀ1; MS m/z 382 0M ); high-resolution mass m/z
calcd for C19H17F3O5 0M ) 382.1028, found: 382.1018.
389 0M ); high-resolution mass m/z calcd for C17H18F3O4S
0M ) 389.0908, found: 389.0907.
4.33. Dimethyl 6-.4-fluorophenyl)-5-oxo-3,3a,4,5-
tetrahydro-1H-pentalene-2,2-dicarboxylate .29)
4.29. 6-.4-Trifluoromethylphenyl)-2-tosyl-2,3,3a,4-
tetrahydro-1H-cyclopenta[c]pyrrol-5-one .24)
Mp 124±1258C; 1H NMR d 7.53 02H, dd, J 5:4,
8.7 Hz), 7.06 02H, d, J 8:7 Hz), 3.80, 3.69 0each 3H,
s), 3.61, 3.25 0each 1H, d, J 19:1 Hz), 3.06±3.20 01H,
m), 2.74±2.87 02H, m), 2.26 01H, dd, J 3:2, 18.2 Hz), 1.73
01H, t, J 12:7 Hz); 13C NMR d 206.8, 178.3, 171.8, 171.0,
164.2, 160.6, 134.4, 130.1, 129.6, 115.5, 115.2, 61.1, 53.3,
53.0, 42.8, 42.2, 38.7, 35.9; IR 1742, 1703, 1633, 1601,
Mp 183±1848C; 1H NMR d 7.74, 7.33 0each 2H, d,
J 8:3 Hz), 7.67, 7.60 0each 2H, d, J 8:2 Hz), 4.68,
4.09 0each 1H, d, J 15:2 Hz), 4.11 01H, dd, J 6:5,
10.9 Hz), 3.18±3.32 01H, m), 2.84 01H, dd, J 6:6,
17.9 Hz), 2.67 01H, dd, J 9:6, 10.9 Hz), 2.42 03H, s),
2.30 01H, dd, J 3:6, 17.9 Hz); 13C NMR d 204.8, 174.1,
144.1, 134.8, 133.5, 133.3, 130.3, 130.0, 128.4, 127.3,
125.7, 125.5, 51.8, 48.2, 42.1, 40.5, 21.4; IR 1701, 1638,
1508 cmÀ1; MS m/z 332 0M ); high-resolution mass m/z
calcd for C18H17FO5 0M ) 332.1060, found: 332.1053.
1617, 1600 cmÀ1; MS m/z 421 0M ); high-resolution mass
4.34. Dimethyl 6-.pentafluorophenyl)-5-oxo-3,3a,4,5-
tetrahydro-1H-pentalene-2,2-dicarboxylate .30)
m/z calcd for C21H18F3NO3S 0M ) 421.0960, found:
421.0966.
Mp 1148C; 1H NMR d 3.80, 3.73 0each 3H, s), 3.38, 3.16
0each 1H, d, J 19:4 Hz), 3.20±3.37 01H, m), 2.93 01H, dd,
J 8, 12.8 Hz), 2.83 01H, dd, J 6:3, 18 Hz), 2.34 01H, dd,
J 3:2, 18 Hz), 1.83 01H, t, J 12:8 Hz); 13C NMR d
203.6, 184.9, 171.5, 170.7, 142.5, 139.5, 135.9, 124.4, 60.4,
53.4, 53.2, 41.9, 39.0, 35.4; IR 1746, 1719, 1672, 1653,
4.30. 6-.4-Fluorophenyl)-2-tosyl-2,3,3a,4-tetrahydro-1H-
cyclopenta[c]pyrrol-5-one .25)
Mp 188±1898C; 1H NMR d 7.73, 7.32 0each 2H, d,
J 8:3 Hz), 7.47 02H, dd, J 5:4, 8.6 Hz), 7.10 02H, t,
J 8:6 Hz), 4.61, 4.06 0each 1H, d, J 16:8 Hz), 4.09 01H,
dd, J 6:4, 11.1 Hz), 3.12±3.27 01H, m), 2.79 01H, dd,
J 6:4, 18 Hz), 2.62 01H, dd, J 9:4, 11.1 Hz), 2.41 03H,
s), 2.25 01H, dd, J 3:6, 18 Hz); 13C NMR d 205.3,
171.6, 144.0, 134.9, 133.6, 130.1, 130.0, 127.3, 115.8,
115.5, 51.9, 48.2, 41.8, 40.5, 21.5; IR 1700, 1638, 1594,
1523, 1501 cmÀ1; MS m/z 404 0M ); high-resolution mass
m/z calcd for C18H13F5O5 0M ) 404.0683, found: 404.0696.
4.35. 6-[.4-Trifluoromethylphenyl)-a-hydroxymethyl]-2-
tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one
.31L, H)
1508 cmÀ1; MS m/z 371 0M ); high-resolution mass
m/z calcd for C20H18FNO3S 0M ) 371.0991, found:
371.0985.
31L; mp 146±1488C; 1H NMR d 7.69, 7.35 0each 2H, d,
J 8:3 Hz), 7.57, 7.48 0each 2H, d, J 7:9 Hz), 5.56 01H,