REACTION OF 1-BROMOVINYL AND 1-BROMO-2-PHENYLVINYL SULFONES
1455
–
1
trum, ν, cm : 3048 m, 1736 s, 1728 s, 1709 s, 1439 s,
335 s, 1316 s, 1308 v.s, 1300 v.s, 1265 v.s, 1258 v.s,
3. Crossland, I., Bock, K., and Norrestam, R., Acta Chem.
Scand., 1985, vol. 39, p. 7.
4. Vardapetyan, A.A., Khachatryan, D.S., Panosyan, G.A.,
and Morlyan, N.M., Zh. Org. Khim., 1986, vol. 22,
p. 2262.
1
1
1
123 s, 1115 v.s, 795 m, 698 s, 536 s, 478 s. H NMR
spectrum, δ, ppm: 1.69 d.d (1H, H , J = 5.5, 9.1 Hz),
A
2
3
4
7
.06 d.d (1H, H , J = 5.5, 6.7 Hz), 2.43 s (3H, CH ),
M
3
5
6
7
8
9
. Arai, S., Nakayama, K., Hatano, K., and Shioiri, T.,
.01 d.d (1H, H , J = 6.7, 9.1 Hz), 3.76 s (3H, OCH ),
X
3
J. Org. Chem., 1998, vol. 63, p. 9572.
.34 d and 4.47 d (1H each, CH SO , J = 13.7 Hz),
2
2
. Arai, S., Nakayama, K., Ishida, T., and Shioiri, T.,
Tetrahedron Lett., 1999, vol. 40, p. 4215.
. Farina, F., Maestro, M.C., Martin, M.V., and
Soria, M.L., Tetrahedron, 1987, vol. 43, p. 4007.
. Hagiwara, H., Sato, K., Suzuki, T., and Ando, M.,
Tetrahedron Lett., 1997, vol. 38, p. 2103.
. Hagiwara, H., Sato, K., Nishino, D., Hoshi, T.,
Suzuki, T., and Ando, M., J. Chem. Soc., Perkin
Trans. 1, 2001, p. 2946.
.35–7.41 m (3H, H
), 7.42–7.46 (2H, H
).
arom
arom
1
3
3
C NMR spectrum, δ , ppm: 16.4 (C ), 30.5 (COMe),
C
1
2
4
1
1
0.0 (C ), 41.1 (C ), 53.5 (OMe), 60.6 (CH SO ),
2
2
27.2 weak (C ), 129.0 (2C, C ), 129.2 (C ),
arom
arom
arom
30.9 (2C, C
), 68.3 (C=O), 198.4 (MeC=O).
arom
Found, %: C 56.55; H 5.35; S 10.71. C H O S. Cal-
1
4
16
5
culated, %: C 56.74; H 5.44; S 10.82.
Methyl 2t-(phenylmethanesulfonyl)cyclopropane-
1
1
2
9
1
2
r-carboxylate (XIc). Yield 2%, R 0.13, mp 116–
f
1
0. Yamamoto, I., Sakai, T., Ohto, K., Matsuzaki, K., and
Fukuyama, K., J. Chem. Soc., Perkin Trans. 1, 1985,
p. 2785.
–
1
17°C (from EtOAc–hexane). IR spectrum, ν, cm :
947 w, 1732 v.s, 1319 s, 1296 s, 1223 s, 1130 s,
1
10 m, 729 m, 702 m. H NMR spectrum, δ, ppm:
1
1. Vasin, V.A., Bolusheva, I.Yu., Razin, V.V., and
.32–1.38 m (1H, H ), 1.96–2.01 m (1H, H ), 2.19–
A
Y
Somov, N.V., Russ. J. Org. Chem., 2014, vol. 50, p. 993.
.25 m (1H, H ), 2.38–2.44 m (1H, H ), 3.80 s (3H,
X
M
1
1
2. Vasin, V.A., Bolusheva, I.Yu., and Razin, V.V., Chem.
CH ), 4.30 d and 4.42 d (1H each, CH SO , J =
3
2
2
Heterocycl. Compd., 2008, vol. 44, no. 4, p. 419.
1
3.7 Hz), 7.35–7.42 m (3H, H ), 7.46–7.53 (2H,
arom
3. Yamamoto, I., Saluchi, N., Futaesaku, N., Fujimoto, K.,
Fujimoto, T., and Ohta, K., J. Chem. Res. (M), 1992,
p. 656.
1
3
3
1
H
). C NMR spectrum, δ , ppm: 8.3 (C ), 15.4 (C ),
arom
C
2
2
2.3 (C ), 52.9 (OMe), 60.2 (CH SO ), 127.8 weak
2
2
(
(
C
), 129.0 (3C, C ), 130.9 (2C, C ), 167.7
arom
arom
arom
14. Evans, P. and Taylor, R.J.K., Synlett, 1997, p. 1043.
C=O). Found, %: C 56.62; H 5.58; S 12.69.
1
5. Alonso, M.E. and Morales, A., J. Org. Chem., 1980,
C H O S. Calculated, %: C 56.68; H 5.55; S 12.61.
1
2
14
4
vol. 45, p. 4530.
Methyl 5-(phenylmethanesulfonyl)-4,5-dihydro-
16. Günther, H., NMR Spectroscopy: An Introduction,
furan-3-carboxylate (Xc). Yield 7%, R 0.27, mp 133–
Chichester: Wiley, 1980, chap. IV.2.
f
–
1
1
2
34°C (from EtOAc–hexane). IR spectrum, ν, cm :
955 w, 1701 v.s, 1662 v.s, 1435 m, 1323 s, 1273 s,
223 s, 1134 s, 1088 s, 1018 m, 760 m, 505 m.
17. Solladie-Cavallo, A. and Isarno, T., Tetrahedron Lett.,
1999, vol. 40, p. 1579.
1
18. Vasin, V.A., Bolusheva, I.Yu., Razin, V.V., and So-
1
H NMR spectrum, δ, ppm: 2.29 d.d (3H, CH , J = 1.4,
mov, N.V., Russ. J. Org. Chem., 2013, vol. 49, p. 1257.
3
1
3
.6 Hz), 3.04–3.15 m and 3.37–3.45 m (1H each, 4-H),
19. Eliel, E.L., Wilen, S.H., and Doyle, M.P., Basic
Organic Stereochemistry, New York: Wiley, 2001.
Translated under the title Osnovy organicheskoi stereo-
khimii, Moscow: Binom. Laboratoriya Znanii, 2007,
p. 453.
.71 s (3H, OCH ), 4.23 d and 4.48 d (1H each,
3
CH SO , J = 14.1 Hz), 5.19 d.d (1H, 5-H, J = 5.5,
2
2
1
3
1
1.0 Hz), 7.37–7.45 m (5H, H ). C NMR spec-
arom
4
trum, δ , ppm: 13.7 (CH ), 28.9 (C ), 51.3 (OCH ),
C
3
3
5
3
20. Evans, P. and Taylor, R.J.K., J. Sulfur Chem., 2005,
5
5.7 (CH SO ), 87.6 (C ), 103.3 (C ), 126.9 weak
2
2
vol. 26, p. 481.
(
C
), 129.1 (2C, C ), 129.2 (C ), 130.9 (2C,
), 164.7 (C ), 166.2 (C=O). Found, %: C 56.82;
arom
arom
arom
2
21. Gaillot, J.-M., Gelas-Mialhe, Y., and Vessière, R., Can.
C
arom
J. Chem., 1979, vol. 57, p. 1958.
2. Harwood, L.M., Julia, M., and Le Thuillier, G., Tetra-
hedron, 1980, vol. 36, p. 2483.
3. Inomata, K., Sasaoka, S., Kobayashi, T., Tanaka, Y.,
Igarashi, S., Ohtani, T., Kinoshita, H., and Kotake, H.,
Bull. Chem. Soc. Jpn., 1987, vol. 60, p. 1767.
H 5.41; S 10.71. C H O S. Calculated, %: C 56.74;
H 5.44; S 10.82.
1
4
16
5
2
2
REFERENCES
1
2
. Verhé, R. and De Kimpe, N., The Chemistry of the
Cyclopropyl Group, Patai, S. and Rappoport, Z., Eds.,
24. Carlier, P., Gelas-Mialhe, Y., and Vessière, R., Can. J.
Chichester: Wiley, 1987, vol. 1, chap. 9, p. 445.
Chem., 1977, vol. 55, p. 3190.
. Joucla, M. and Le Brun, J., Tetrahedron Lett., 1985,
vol. 26, p. 3001.
25. Makosza, M., Podraza, R., and Bialecki, M., Gazz.
Chim. Ital., 1995, vol. 125, p. 601.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 10 2014