-
3
-
-
34250731005
-
-
Schaumann, E, Ed, Thieme: Stuttgart
-
(c) Schukat, G.; Fanghänel, E. In Science of Synthesis, Vol. 11; Schaumann, E., Ed.; Thieme: Stuttgart, 2002, 191.
-
(2002)
Science of Synthesis
, vol.11
, pp. 191
-
-
Schukat, G.1
Fanghänel, E.2
-
6
-
-
10344244501
-
-
(c) Fabre, J. M. Chem. Rev. 2004, 104, 5133.
-
(2004)
Chem. Rev
, vol.104
, pp. 5133
-
-
Fabre, J.M.1
-
8
-
-
2742604027
-
-
(b) Mayer, R.; Fabian, K.; Kröber, H.; Hartmann, H. J. Prakt. Chem. 1972, 314, 240.
-
(1972)
J. Prakt. Chem
, vol.314
, pp. 240
-
-
Mayer, R.1
Fabian, K.2
Kröber, H.3
Hartmann, H.4
-
9
-
-
34249970549
-
-
(c) Kreitsberga, Y. N.; Vilyuma, E. V.; Khodorkovskii, V. Y.; Neiland, O. Y. Chem. Heterocycl. Comp. (Engl. Transl.) 1988, 1339.
-
(1988)
Chem. Heterocycl. Comp. (Engl. Transl.)
, pp. 1339
-
-
Kreitsberga, Y.N.1
Vilyuma, E.V.2
Khodorkovskii, V.Y.3
Neiland, O.Y.4
-
11
-
-
34250735825
-
-
(b) Minkin, V. I.; Nivorozhkin, L. E.; Trofimova, N. S.; Revinskii, Y. V.; Knyazhanskii, M. I.; Volbushko, N. V.; Osipov, O. A.; Lukash, A. V.; Simkin, B. Y. J. Org. Chem. USSR 1975, 11, 818.
-
(1975)
J. Org. Chem. USSR
, vol.11
, pp. 818
-
-
Minkin, V.I.1
Nivorozhkin, L.E.2
Trofimova, N.S.3
Revinskii, Y.V.4
Knyazhanskii, M.I.5
Volbushko, N.V.6
Osipov, O.A.7
Lukash, A.V.8
Simkin, B.Y.9
-
12
-
-
0001821268
-
-
Simonsen, K. B.; Geisler, T.; Petersen, J. C.; Arentoft, J.; Sommer-Larsen, P.; Rodriguez Greve, D.; Jakobsen, C.; Becher, J.; Malagolid, M.; Brédas, J. L.; Bjørnholm, T. Eur. J. Org. Chem. 1998, 2747.
-
(1998)
Eur. J. Org. Chem
, pp. 2747
-
-
Simonsen, K.B.1
Geisler, T.2
Petersen, J.C.3
Arentoft, J.4
Sommer-Larsen, P.5
Rodriguez Greve, D.6
Jakobsen, C.7
Becher, J.8
Malagolid, M.9
Brédas, J.L.10
Bjørnholm, T.11
-
15
-
-
34250733198
-
-
6b
-
6b
-
-
-
-
16
-
-
34250711533
-
-
Thione 1a is commercially available,
-
(a) Thione 1a is commercially available,
-
-
-
-
17
-
-
0000132833
-
-
Compounds 1b and 1c were prepared according to: Haley, N. F.; Fichtner, M. W. J. Org. Chem. 1980, 45, 175.
-
(b) Compounds 1b and 1c were prepared according to: Haley, N. F.; Fichtner, M. W. J. Org. Chem. 1980, 45, 175.
-
-
-
-
18
-
-
34250780178
-
-
Compound 1d was prepared according to: Steimecke, G.; Sieler, H.-J.; Kirmse, R.; Hoyer, E. Phosphorus Sulfur Relat. Elem. 1979, 7, 49.
-
(c) Compound 1d was prepared according to: Steimecke, G.; Sieler, H.-J.; Kirmse, R.; Hoyer, E. Phosphorus Sulfur Relat. Elem. 1979, 7, 49.
-
-
-
-
19
-
-
37049161214
-
-
Compound 2a: Challenger, F.; Mason, E. A.; Holdsworth, E. C.; Emmott, R. J. Chem. Soc 1953, 292.
-
(a) Compound 2a: Challenger, F.; Mason, E. A.; Holdsworth, E. C.; Emmott, R. J. Chem. Soc 1953, 292.
-
-
-
-
20
-
-
0026062219
-
-
Compounds 2b-d: Moore, A. J.; Bryce, M. R. Synthesis 1991, 26.
-
(b) Compounds 2b-d: Moore, A. J.; Bryce, M. R. Synthesis 1991, 26.
-
-
-
-
22
-
-
34250724612
-
-
2) in the case of 3c.
-
2) in the case of 3c.
-
-
-
-
23
-
-
34250701857
-
-
Some of these isopropylidene malonates had already been prepared under different conditions than those described here, but their reported melting points3c are lower than those measured by us. Therefore, full characterization data for compounds 3 follow: Compound 3a: yield 69, mp 244-245°C (lit.3c 235-237°C, IR (Nujol, 1651 cm-1. 1H NMR (400 MHz, DMSO-d6, δ, 7.97 (s, 2 H, 1.66 (s, 6 H, 13C NMR (100 MHz, DMSO-d 6, δ, 182.0, 161.1, 1284, 103.8, 93.4, 26.3. MS (EI, m/z, 244 (60, Compound 3b: yield 76, mp 219-220°C (lit.3c 208-210°C, IR (Nujol, 1665 cm-1. 1H NMR (300 MHz, CDCl3, δ, 2.30 (s, 6 H, 1.70 (s, 6 H, 13C NMR (100 MHz, CDCl3, δ, 179.4, 162.1, 132.7, 104.2, 93.4, 26.9, 13.1. MS (EI, m/z, 272 70, Compound 3c: yield 68
-
3): δ = 179.4, 161.6, 135.2, 104.6, 26.9, 19.2. MS (EI): m/z (%) = 336 (95).
-
-
-
-
24
-
-
0038805340
-
-
(a) Wilt, J. R.; Reynolds, G. A.; Van Allan, J. A. Tetrahedron 1973, 29, 795.
-
(1973)
Tetrahedron
, vol.29
, pp. 795
-
-
Wilt, J.R.1
Reynolds, G.A.2
Van Allan, J.A.3
-
25
-
-
0001508446
-
-
(b) Weidner, C. H.; Wadsworth, D. H.; Bender, S. L.; Beltman, D. J. J. Org. Chem. 1989, 54, 3660.
-
(1989)
J. Org. Chem
, vol.54
, pp. 3660
-
-
Weidner, C.H.1
Wadsworth, D.H.2
Bender, S.L.3
Beltman, D.J.4
-
26
-
-
0032762850
-
-
(c) Yagi, S.; Maeda, K.; Nakazumi, H. J. Mater. Chem. 1999, 9, 2991.
-
(1999)
J. Mater. Chem
, vol.9
, pp. 2991
-
-
Yagi, S.1
Maeda, K.2
Nakazumi, H.3
-
27
-
-
34250765019
-
-
2O, dried, and optionally recrystallized from AcOH. In the case of 4d we have not been able to completely purify the desired salt.
-
2O, dried, and optionally recrystallized from AcOH. In the case of 4d we have not been able to completely purify the desired salt.
-
-
-
-
28
-
-
34250757836
-
-
Compound 4a: yield 82, mp 109-110°C. 1H NMR (300 MHz, CF3COOD, δ, 8.92 (s, 2 H, 3.43 (s, 3 H, 13C NMR (75 MHz, CF3COOD, δ, 204.3, 145.1, 20.6. MS (MALDI, dithranol, m/z, 117 [C4H5S2, Compound 4b: yield 87, mp 50-51°C (dec, 1H NMR (300 MHz, CDCl3, δ, 3.28 (s, 3 H, 2.69 (s, 6 H, 13C NMR (100 MHz, CDCl3, δ, 193.9, 151.4, 19.5, 14.3. MS (MALDI, dithranol, m/z, 145 [C6H9S2, Compound 4c: yield 84, mp 129-132°C. 1H NMR (300 MHz, CF 3COOD, δ, 8.73 (s, 1 H, 7.69-7.52 (m, 5 H, 3.40 (s, 3 H, 13C NMR (75 MHz, CF3COOD, δ, 202.0, 135.9, 135.2, 132.6, 129.9, 20.6. MS (MALDI, dithranol, m/z, 193 [C 10H9S2, Compound 4d: 1H NMR 400 MHz, C
-
4].
-
-
-
-
29
-
-
0001093961
-
-
3N: (a) Wadsworth, D. H.; Detty, M. R.; Murray, B. J.; Weidner, C. H.; Haley, N. F. J. Org. Chem. 1984, 49, 2676.
-
3N: (a) Wadsworth, D. H.; Detty, M. R.; Murray, B. J.; Weidner, C. H.; Haley, N. F. J. Org. Chem. 1984, 49, 2676.
-
-
-
-
31
-
-
0037450490
-
-
(c) Leriche, P.; Roquet, S.; Pillerel, N.; Mabon, G.; Frère, P. Tetrahedron Lett. 2003, 44, 1623.
-
(2003)
Tetrahedron Lett
, vol.44
, pp. 1623
-
-
Leriche, P.1
Roquet, S.2
Pillerel, N.3
Mabon, G.4
Frère, P.5
-
33
-
-
0141631819
-
-
(a) Andreu, R.; Garín, J.; Orduna, J.; Alcalá, R.; Villacampa, B. Org. Lett. 2003, 5, 3143.
-
(2003)
Org. Lett
, vol.5
, pp. 3143
-
-
Andreu, R.1
Garín, J.2
Orduna, J.3
Alcalá, R.4
Villacampa, B.5
-
34
-
-
20944433734
-
-
(b) Andreu, R.; Blesa, M. J.; Carrasquer, L.; Gariń, J.; Orduna, J.; Villacampa, B.; Alcalá, R.; Casado, J.; Ruiz Delgado, M. C.; Lópe Navarrete, J. T.; Allain, M. J. Am. Chem. Soc. 2005, 127, 8835.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 8835
-
-
Andreu, R.1
Blesa, M.J.2
Carrasquer, L.3
Gariń, J.4
Orduna, J.5
Villacampa, B.6
Alcalá, R.7
Casado, J.8
Ruiz Delgado, M.C.9
Lópe Navarrete, J.T.10
Allain, M.11
-
36
-
-
34250761108
-
-
2O, dried, and recrystallized from AcOH if necessary.
-
2O, dried, and recrystallized from AcOH if necessary.
-
-
-
-
37
-
-
34250737595
-
-
Compound 5a: yield 59, mp 161-162°C IR (Nujol, 1625 cm -1. 1H NMR (400 MHz, DMSO-d6, δ, 8.38 (d, 1 H, J, 11.8 Hz, 7.57 (s, 2 H, 6.91 (d, 1 H, J, 11.8 Hz, 3.41 (s, 3 H, 3.19 (s, 3 H, 13C NMR (100 MHz, DMSO-d6, δ, 181.9, 157.8, 125.8, 99.1, 46.4. MS-FAB: m/z, 172 [C7H10NS2, Compound 5b: yield 65, mp 193-194°C. IR (Nujol, 1630 cm-1. 1H NMR (300 MHz, DMSO-d6, δ, 8.33 (d, 1 H, J, 11.8 Hz, 6.84 (d, 1 H, J, 11.8 Hz, 3.40 (s, 3 H, 3.18 (s, 3 H, 2.23 (s, 6 H, 13C NMR (100 MHz, DMSO-d6, δ, 183.2, 162.6, 134.7, 104.1, 51.7, 44.3, 18.5, 18.1. MS (MALDI, dithranol, m/z, 200 [C9H14NS2, Compound 5c: yield 40, mp 224°C (dec, darkening from 175°C, IR Nujol, 1626 cm
-
2].
-
-
-
-
38
-
-
0001063982
-
-
Scheibe, G.; Seiffert, W.; Hohlneicher, G.; Jutz, Ch.; Springer, H. J. Tetrahedron Lett. 1966, 7, 5053.
-
(1966)
Tetrahedron Lett
, vol.7
, pp. 5053
-
-
Scheibe, G.1
Seiffert, W.2
Hohlneicher, G.3
Jutz, C.4
Springer, H.J.5
-
41
-
-
4744344728
-
-
Andreu, R.; Garín, J.; López, C.; Orduna, J.; Levillain, E. Tetrahedron Lett. 2004, 45, 8211.
-
(2004)
Tetrahedron Lett
, vol.45
, pp. 8211
-
-
Andreu, R.1
Garín, J.2
López, C.3
Orduna, J.4
Levillain, E.5
|