Phenyl 3-Methylpentyl Sulfone (2b): from R-I; yield,
80%; oil. 1H NMR δ 7.88 (d, J ) 7.2 Hz, 2H), 7.61-7.64 (m, 1H),
7.52-7.56 (m, 2H), 2.98-3.12 (m, 2H), 1.65-1.74 (m, 1H), 1.45-
1.54 (m, 1H), 1.34-1.42 (m, 1H), 1.20-1.29 (m, 1H), 1.06-1.15
(m, 1H), 0.77-0.82 (m, 6H); 13C NMR δ 139.3, 133.7, 129.3,
128.1, 54.5, 33.5, 29.0, 28.8, 18.8, 11.2; Anal. Calcd for
C12H18O2S: C, 63.68; H, 8.02. Found: C, 63.55; H, 8.16.
Phenyl 3,3-Dimethylbutyl Sulfone (2c): from R-I; yield,
Ethyl Hexanesulfonate (4d): from R-I; yield, 83%; oil. 1H
NMR δ 4.28 (q, J ) 7.2 Hz, 2H), 3.07 (t, J ) 8.0 Hz, 2H), 1.81-
1.89 (m, 2H), 1.38-1.46 (m, 2H), 1.40 (t, J ) 7.2 Hz, 3H), 1.28-
1.35 (m, 4H), 0.90 (t, J ) 7.2 Hz, 3H); 13C NMR δ 66.0, 50.7,
31.3, 28.0, 23.6, 22.4, 15.3, 14.1.
Sulfonamides.
N,N-Diethyl Hexanesulfonamide (5a): from R-I; yield,
88%; oil. 1H NMR δ 3.30 (q, J ) 7.2 Hz, 4H), 2.91 (t, J ) 8.0 Hz,
2H), 1.75-1.83 (m, 2H), 1.37-1.44 (m, 2H), 1.28-1.34 (m, 4H),
1.21 (t, J ) 7.2 Hz, 6H), 0.90 (t, J ) 6.8 Hz, 3H); 13C NMR δ
52.6, 41.7, 31.5, 28.3, 23.7, 22.6, 14.7, 14.2; Anal. Calcd for
C10H23NO2S: C, 54.26; H, 10.47; N, 6.33. Found: C, 54.35; H,
10.52; N, 6.18.
1
91% white solid, mp 65.6-66.3 °C. H NMR δ 7.93 (d, J ) 7.6
Hz, 2H), 7.65-7.69 (m, 1H), 7.57-7.61 (m, 2H), 3.05-3.09 (m,
2H), 1.59-1.64 (m, 2H), 0.98 (s, 9 H); 13C NMR δ 139.3, 133.7,
129.4, 128.1, 53.0, 35.7, 30.1, 29.0; Anal. Calcd for C12H18O2S:
C, 63.68; H, 8.02. Found: C, 63.84; H, 8.10.
Phenyl 4-Phenylbutyl Sulfone (2d): from R-I; yield, 59%;
white solid, mp 74.9-75.4 °C. 1H NMR δ 7.88-7.92 (m, 2 H),
7.64-7.69 (m, 1H), 7.55-7.59 (m, 2H), 7.24-7.28 (m, 2H), 7.16-
7.20 (m, 1H), 7.11 (d, J ) 7.2 Hz, 2H), 3.11 (t, J ) 7.2 Hz, 2H),
2.60 (t, J ) 7.2 Hz, 2H), 1.67-1.82 (m, 4H); 13C NMR δ 141.4,
139.4, 133.8, 129.5, 128.6, 128.5, 128.3, 126.2, 56.3, 35.5, 30.2,
22.5; Anal. Calcd for C16H18O2S: C, 70.04; H, 6.62; S, 11.69.
Found: C, 70.04; H, 6.61; S, 11.99.
N,N-Diethyl 3-Methylpentanesulfonamide (5b): from R-I;
1
yield, 83%; oil. H NMR δ 3.30 (q, J ) 7.2 Hz, 4H), 2.85-2.99
(m, 2H), 1.77-1.87 (m, 1H), 1.56-1.66 (m, 1H), 1.41-1.50 (m,
1H), 1.30-1.41 (m, 1H), 1.17-1.24 (m, 1H), 1.21 (t, J ) 7.2 Hz,
6H), 0.91 (d, J ) 7.1 Hz, 3H), 0.90 (t, J ) 7.2 Hz, 3H); 13C NMR
δ 50.6, 41.7, 33.7, 29.8, 29.1, 18.9, 14.6, 11.3; Anal. Calcd for
C10H23NO2S: C, 54.26; H, 10.47; N, 6.33. Found: C, 54.23; H,
10.52; N, 6.27.
Ethyl 4-Phenylbutyl Sulfone (2e): from R-I; yield, 77%;
oil. 1H NMR δ 7.27-7.32 (m, 2H), 7.17-7.23 (m, 3H), 2.94-2.99
(m, 4H), 2.68 (t, J ) 7.6 Hz, 2H), 1.85-1.93 (m, 2H), 1.76-1.84
(m, 2H), 1.39 (t, J ) 7.6 Hz, 3H); 13C NMR δ 141.4, 128.7, 128.6,
N,N-Diethyl 3,3-Dimethylbutanesulfonamide (5c): from
1
R-I; yield, 94%; oil. H NMR δ 3.31 (q, J ) 7.2 Hz, 4H), 2.89-
2.93 (m, 2H), 1.66-1.70 (m, 2H), 1.21 (t, J ) 7.2 Hz, 6H), 0.93
(s, 9H); 13C NMR δ 49.2, 41.7, 36.9, 30.3, 29.3, 14.7; Anal. Calcd
for C10H23NO2S: C, 54.26; H, 10.47; N, 6.33; S, 14.49. Found:
C, 54.04; H, 10.55; N, 6.06; S, 14.81.
126.3, 52.0, 47.3, 35.5, 30.4, 21.7, 6.8; Anal. Calcd for C12H18
-
O2S: C, 63.68; H, 8.02; S, 14.17. Found: C, 63.32; H, 8.24; S,
14.31.
N-Benzyl 5-Ethoxycarbonylpentanesulfonamide (5g):
from R-Br; yield, 85%; white solid, mp 45.5-45.9 °C. 1H NMR
δ 7.29-7.41 (m, 5H), 4.48 (br, t, J ) 6.8 Hz, 1H), 4.31 (d, J )
6.8 Hz, 2H), 4.13 (q, J ) 7.2 Hz, 2H), 2.93 (t, J ) 7.2 Hz, 2H),
2.29 (t, J ) 7.2 Hz, 2H), 1.75-1.82 (m, 2H), 1.58-1.65 (m, 2H),
1.36-1.44 (m, 2H), 1.27 (d, J ) 7.2 Hz, 3H); 13C NMR δ 173.6,
137.4, 129.1, 128.3, 128.1, 60.6, 53.3, 47.4, 34.0, 27.8, 24.5, 23.5,
14.4; Anal. Calcd for C15H23NO4S: C, 57.48; H, 7.40; N, 4.47.
Found: C, 57.46; H, 7.42; N, 4.44.
N-Benzyl 4-Phenoxybutanesulfonamide (5h): from R-Br;
66%; white solid; mp 85.0-86.0 °C. 1H NMR δ 7.38-7.27 (m,
5H), 7.27-7.32 (m, 2H), 6.96 (t, J ) 7.2 Hz, 1H), 6.87 (d, J )
9.2 Hz, 2H), 4.47 (br, t, J ) 6.8 Hz, 1H), 4.32 (d, J ) 6.8 Hz,
2H), 3.95 (t, J ) 6.0 Hz, 2H), 3.03 (t, J ) 7.6 Hz, 2H), 1.95-2.03
(m, 2H), 1.83-1.90 (m, 2H); 13C NMR δ 158.9, 137.1, 129.7,
129.1, 128.3, 128.2, 121.1, 114.7, 67.0, 53.2, 47.4, 28.0, 21.0; Anal.
Calcd for C17H21NO3S: C, 63.92; H, 6.63; N, 4.39. Found: C,
63.76; H, 6.42; N, 4.24.
N-Benzyl 5-(1H-Pyrrol-1-yl)-pentanesulfonamide (5i):
from R-Br; yield, 88%; oil. 1H NMR δ 7.29-7.39 (m, 5H), 6.62-
6.65 (m, 2H), 6.13-6.16 (m, 2H), 4.49 (br t, J ) 6.0 Hz, 1H),
4.29 (d, J ) 6.0 Hz, 2H), 3.87 (t, J ) 7.2 Hz, 2H), 2.89 (t, J ) 8.0
Hz, 2H), 1.71-1.79 (m, 4H), 1.30-1.38 (m, 2H); 13C NMR δ
137.0, 129.1, 128.4, 128.2, 120.7, 108.3, 53.4, 49.3, 47.5, 31.2,
25.6, 23.5; Anal. Calcd for C16H22N2O2S: C, 62.71; H, 7.24; N,
9.14. Found: C, 62.67; H, 7.30; N, 9.06.
Phenyl 6,6,6-Trifluorohexyl Sulfone (2m): from R-Br;
1
yield, 80%; oil. H NMR δ 7.90 (d, J ) 8.0 Hz, 2H), 7.65-7.69
(m, 1H), 7.57-7.61 (m, 2H), 3.10 (t, J ) 8.4 Hz, 2H), 1.99-2.11
(m, 2H), 1.73-1.80 (m, 2H), 1.43-1.57 (m, 4H); 13C NMR δ 139.4,
1
134.0, 129.6, 128.2, 127.3 (q, JC-F ) 276.0 Hz), 56.1, 33.6 (q,
2JC-F ) 29.0 Hz), 27.6, 22.6, 21.7; Anal. Calcd for C12H15F3O2S:
C, 51.42; H, 5.39. Found: C, 51.12; H, 5.33.
Phenyl 3-(2-Tetrahydrafuranyl)propyl Sulfone (2n): from
R-Br; yield, 62%; oil. 1H NMR δ 7.90 (d, J ) 8.0 Hz, 2H), 7.64-
7.68 (m, 1H), 7.56-7.60 (m, 2H), 3.73-3.84 (m, 2H), 3.65-3.72
(m, 1H), 3.09-3.23 (m, 2H), 1.92-2.00 (m, 1H), 1.77-1.89 (m,
4H), 1.55-1.62 (m, 2H), 1.38-1.46 (m, 1H); 13C NMR δ 139.2,
133.7, 129.3, 128.1, 78.5, 67.8, 56.3, 34.1, 31.4, 25.7, 20.0.
Phenyl 4-Cyanobutyl Sulfone (2o): from R-Br, yield, 72%;
white solid; mp 58.5-59.3 °C. 1H NMR δ 7.93 (d, J ) 7.6 Hz,
2H), 7.68-7.71 (m, 1H), 7.58-7.62 (m, 2H), 3.14 (t, J ) 7.2 Hz,
2H), 2.39 (t, J ) 6.8 Hz, 2H), 1.88-1.96 (m, 2 H), 1.79-1.86 (m,
2H); 13C NMR δ 138.7, 133.9, 129.3, 127.9, 118.9, 55.0, 23.9, 21.8,
16.7; Anal. Calcd for C11H13NO2S: C, 59.17; H, 5.87; N, 6.27.
Found: C, 58.96; H, 5.68; N, 5.98.
Sulfonates.
Phenyl 3-Methylpentanesulfonate (4a): from R-I; yield,
84%; oil. 1H NMR δ 7.40-7.44 (m, 2H), 7.27-7.34 (m, 3H), 3.15-
3.31 (m, 2H), 1.95-2.06 (m, 1H), 1.75-1.85 (m, 1H), 1.49-1.60
(m, 1H), 1.34-1.44 (m, 1H), 1.18-1.29 (m, 1H), 0.94 (d, J ) 6.4
Hz, 3H), 0.92 (t, J ) 7.2 Hz, 3H); 13C NMR δ 149.4, 130.1, 127.3,
122.3, 48.9, 33.6, 29.9, 29.1, 18.9, 11.3.
Acknowledgment. We dedicate this paper to Pro-
fessor Iwao Ojima on the occasion of his 60th birthday.
We thank Pete Dormer and Robert Reamer for NMR
assistance.
Phenyl 3,3-Dimethylbutanesulfonate (4b): from R-I;
yield, 85%; oil. 1H NMR δ 7.41-7.44 (m, 2H), 7.23-7.34 (m, 3H),
3.21-3.26 (m, 2H), 1.87-1.92 (m, 2H), 0.97 (s, 9H); 13C NMR δ
149.4, 130.2, 127.4, 122.2, 47.4, 36.8, 30.4, 29.1; Anal. Calcd for
C12H18O3S: C, 59.47; H, 7.49. Found: C, 59.36; H, 7.62.
Phenyl 5-Cyanopentanesulfonate (4c): from R-Br; 72%
yield; oil. 1H NMR δ 7.42-7.45 (m, 2H), 7.32-7.36 (m, 1H), 7.28
(d, J ) 8.4 Hz, 2H), 3.28 (t, J ) 7.6 Hz, 2H), 2.41 (t, J ) 6.8 Hz,
2H), 2.00-2.08 (m, 2H), 1.64-1.79 (m, 4H); 13C NMR δ 149.2,
130.2, 127.4, 122.1, 119.3, 50.1, 27.2, 25.0, 23.0, 17.0.
Supporting Information Available: Characterization
data including 1H, 13C, and elemental analysis for 2f-2k, 2p-
2v, and 4e-4j, and 5d-5f. This material is available free of
JO050500G
J. Org. Chem, Vol. 70, No. 17, 2005 6947