K. Sato et al. / Tetrahedron 57 (2001) 2469±2476
2475
1
H). C NMR (100 MHz, CDCl ) d 127.65, 129.26,
33.15, 141.61.
3
4
1
Research (No. 07CE2004) from the Ministry of Education,
Science, Sports and Culture of Japan.
3
4
2
6
.7.7. 4,6-Dimethyldibenzothiophene-5,5-dioxide. Mp
1
44.0±244.58C. H NMR (400 MHz, CDCl ) d 2.71 (s,
3
H), 7.24 (d, 2H, J7.6 Hz), 7.47 (t, 2H, J7.6 Hz), 7.57
References
1
3
(
1
d, 2H, J7.6 Hz). C NMR (100 MHz, CDCl ) d 16.85,
3
18.75, 131.89, 132.06, 133.39, 135.68, 135.71. HRMS
1. (a) Hollingworth, G. J. Comprehensive Organic Functional
Group Transformations; Katritzky, A. R., Meth-Cohn, O.,
Rees, C. W., Pattenden, G., Eds.; Elsevier: Oxford, 1995;
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Sulphones, Sulphoxides, and Cyclic Sulphides; Patai, S.,
Rappoport, Z., Eds.; Wiley: New York, 1994. (c) Simpkins,
N. S. In Sulphones in Organic Synthesis; Baldwin, J. E.,
Magnus, P. D., Eds.; Pergamon: Oxford, 1993; pp 5±99.
1
1
(
EI ) m/z Calcd for C H O S (M ): 244.0558. Found:
14 12 2
2
44.0556.
6
.7.8. Di-p-nitrophenyl sulfone. Mp 271.0±271.58C. H
2
1
4
NMR (400 MHz, CDCl ) d 8.16±8.19 (m, 4H), 8.38±8.41
3
1
3
(
m, 4H). C NMR (100 MHz, CDCl ) d 124.88, 129.43,
3
145.76, 150.89.
(d) March, J. In Advanced Organic Chemistry; 4th ed.;
Wiley: New York, 1992; pp 1202±1203. (e) Hudlicky, M.
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63 1
.7.9. Diallyl sulfone. H NMR (400 MHz, CDCl ) d 3.72
4
(
3
d, 4H, J7.6 Hz), 5.45 (dd, 2H, J1.2, 16.8 Hz), 5.52 (dd,
2
H, J1.2, 10.4 Hz), 5.93 (tdd, 2H, J7.6, 10.4, 16.8 Hz).
186; American Chemical Society: Washington, DC, 1990;
pp 252±261.
1
3
C NMR (100 MHz, CDCl ) d 55.92, 124.79, 124.83.
3
2
. (a) Clark, E. Kirk-Othmer Encyclopedia of Chemical Tech-
nology; 4th ed.; Kroschwitz, J. I., Howe-Grant, M., Eds.;
Wiley: New York, 1997; Vol. 23, pp 134±146. (b) Willer,
R. Kirk-Othmer Encyclopedia of Chemical Technology; 4th
ed.; Kroschwitz, J. I., Howe-Grant, M., Eds.; Wiley: New
York, 1997; Vol. 23, pp 217±232. (c) Roy, K.-M. Ullmann's
Encyclopedia of Industrial Chemistry; 5th ed.; Elvers, B.,
Hawkins, S., Russey, W., Eds.; VCH: Weinheim, 1994; Vol.
A25, pp 487±501.
6
4
1
4
(
5
7
(
.7.10. 2-Hydroxyethyl phenyl sulfone.
H NMR
400 MHz, CDCl ) d 2.04 (br, 1H), 3.35 (t, 2H, J
3
.2 Hz), 4.01 (t, 2H, J5.2 Hz), 7.60 (t, 2H, J7.6 Hz),
1
3
.68±7.72 (m, 1H), 7.95 (d, 2H, J7.6 Hz). C NMR
100 MHz, CDCl ) d 56.33, 58.24, 127.95, 129.47,
3
1
34.07, 138.94.
4
4
6
1
.7.11. 2-Hydroxypropyl phenyl sulfone. Mp 44.0±
1
6.08C. H NMR (400 MHz, CDCl ) d 1.25 (d, 3H, J
3
3
4
5
6
7
8
9
. Mckillop, A.; Tarbin, J. A. Tetrahedron Lett. 1983, 24, 1505±
1
.4 Hz), 3.16±3.29 (m, 2H), 3.46 (s, 1H), 4.30±4.36 (m,
H), 7.58±7.62 (m, 2H), 7.67±7.71 (m, 1H). 7.92±7.95
508.
. Khurana, J. M.; Panda, A. K.; Ray, A.; Gogia, A. Org. Prep.
Proc. 1996, 28, 234±237.
1
3
(
m, 2H). C NMR (100 MHz, CDCl ) d 22.52, 62.27,
3
1
3.27, 127.81, 129.39, 133.99, 139.10. HRMS (FAB )
6
m/z Calcd for C H NaO S ([M1Na] ): 223.0405. Found:
. Weber, J. V.; Schneider, M.; Salami, B.; Paquer, D. Recl.
Trav. Chim. Pays-Bas 1986, 105, 99±102.
1
9
12
3
223.0415.
. Barton, D. H. R.; Li, W.; Smith, J. A. Tetrahedron Lett. 1998,
39, 7055±7058.
. Kennedy, R. J.; Stock, A. M. J. Org. Chem. 1960, 25, 1901±
6
.7.12. Geranyl phenyl sulfone. Mp 43.0±45.08C. H
5
1
4
NMR (400 MHz, CDCl ) d 1.31 (s, 3H), 1.58 (s, 3H),
3
1
906.
1
(
.68 (s, 3H), 2.00 (s, 4H), 3.80 (d, 2H, J8.0 Hz), 5.02
. Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 1287±
1290.
. Goheen, D. W.; Bennett, C. F. J. Org. Chem. 1961, 26, 1331±
m, 1H), 5.18 (t, 1H, J8.0 Hz) 7.51±7.55 (m, 2H), 7.61±
1
.65 (m, 1H). 7.85±7.88 (m, 2H). C NMR (100 MHz,
3
7
CDCl ) d 16.13, 17.65, 25.66, 26.17, 39.65, 56.08, 110.28,
3
1
333.
0. Ho, T.-L.; Wong, C. M. Synthesis 1972, 561±562.
11. Leonard, N. J.; Johnson, C. R. J. Org. Chem. 1962, 27, 282±
84.
12. Varma, R. S.; Saini, R. K.; Meshram, H. M. Tetrahedron Lett.
997, 38, 6525±6528.
3. Edwards, D.; Stenlake, J. B. J. Chem. Soc. 1954, 3272±3274.
14. Gokel, G. W.; Gerdes, H. M.; Dishong, D. M. J. Org. Chem.
980, 45, 3634±3639.
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840.
1
23.41, 128.55, 128.91, 132.06, 133.49, 138.64, 146.36.
1
6
.7.13. Dibutyl sulfoxide. Mp 34.0±34.58C. H NMR
6
1
4
(
2
400 MHz, CDCl ) d 0.97 (t, 6H, J7.4 Hz), 1.41±1.57
3
1
3
(m, 4H), 1.72±1.79 (m, 4H), 2.60±2.73 (m, 4H).
NMR (100 MHz, CDCl ) d 13.64, 22.05, 24.56, 52.13.
C
1
3
1
6
7
1
.7.14. Methyl phenyl sulfoxide. Mp 30.0±30.58C. H
4
NMR (400 MHz, CDCl ) d 2.73 (s, 3H), 7.48±7.56 (m,
1
3
1
H), 7.64±7.67 (m, 2H). C NMR (100 MHz, CDCl ) d
3
3
4
3
3
3.95, 123.47, 129.33, 131.00, 145.72.
1
1
1
1
2
6. Venier, C. G.; Squires, T. G.; Chen, Y.-Y.; Hussmann, G. P.;
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7. Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847±
6
.7.15. Diphenyl sulfoxide. Mp 72.0±73.08C. H NMR
400 MHz, CDCl ) d 7.42±7.49 (m, 6H), 7.63±7.66 (m,
3
13
H). C NMR (100 MHz, CDCl ) d 124.77, 129.30,
2
1
4
(
2
853.
8. Adam, W.; Hadjiarapoglou, L. Tetrahedron Lett. 1992, 33,
69±470.
4
1
3
31.03, 145.61.
4
9. Breton, G. W.; Fields, J. D.; Kropp, P. J. Tetrahedron Lett.
1995, 36, 3825±3828.
Acknowledgements
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5043±5046.
This work was supported by a Grant-in-aid for COE