3578
B. Neugnot et al. / Tetrahedron 60 (2004) 3575–3579
3. Breederveld, H. Recl. Trav. Chim. Pays-Bas 1960, 79,
4.2.7.
(E)-2-Propenyl-isoindole-1,3-dione.
Rf¼0.55
1
401–407.
(pentane/Et2O 80/20). H NMR (d, ppm): 7.88–7.81 (m,
2H); 7.75–7.69 (m, 2H); 6.64–6.5 (m, 2H); 1.84 (m, 3H).
13C NMR (d, ppm): 166.41; 133.96; 131.47; 123.16; 118.11;
117.75; 16.01. MS (EI): 187 (100); 169 (60); 158 (12). IR:
1706; 1606; 1462; 1376; 1321.
4. Ribereau, P.; Delamare, M.; Celanire, S.; Queguiner, G.
Tetrahedron Lett. 2001, 42, 3571–3573.
5. Beak, P.; Lee, B. J. Org. Chem. 1989, 54, 458–464.
6. Tischler, A. N.; Tischler, M. H. Tetrahedron Lett. 1978, 37,
3407–3410.
4.2.8. (E)-1-Propenyl-pyrrolidine-2,5-dione. Rf¼0.18
7. (a) Lantzsch, R. Eur. Pat. Appl. EP 748798, A1 19961218,
1996. (b) Bortolussi, M.; Bloch, R.; Conia, J. M. Tetrahedron
Lett. 1977, 26, 2289–2292.
1
(pentane/Et2O 30/70). H NMR (d, ppm): 6.57 (qd, 1H,
3
4
3J3H¼6.7 Hz, J1H¼14.6 Hz); 6.42 (qd, 1H, J3H¼1.8 Hz,
3J1H¼14.6 Hz); 2.72 (s, 4H); 1.78 (dd, 3H, J1H¼1.8 Hz,
4
8. (a) Zhang, S. W.; Mitsudo, T.; Kondo, T.; Watanabe, Y.
J. Organomet. Chem. 1995, 485, 55–62. (b) Krompiec, S.
Isomerization of alkenes and their functionally substituted
derivatives catalyzed by ruthenium complexes. Zesz. Nauk.
Pol. 1 1997, 136, 1–174. (c) Cadot, C.; Dalko, P. I.; Cossy, J.
Tetrahedron Lett. 2002, 43, 1839–1841. (d) Dominguez, G.;
Casarrubios, L.; Rodriguez-Noriega, J.; Perez-Castells, J.
Helv. Chim. Acta 2002, 85, 2856–2861.
3J1H¼6.7 Hz). 13C NMR (d, ppm): 175.64; 120.16; 118.96;
27.93; 16.31. MS (EI): 139 (100); 110 (15); 96 (22); 82 (26);
68 (30); 55 (70). IR: 2944; 1717; 1377; 1188.
4.2.9. N-Benzyl (E)-propenyl-carbamic acid tertiobutyl
1
ester. Rf¼0.6 (pentane/Et2O 95/5). H NMR (in C7D8 at
343 K, d, ppm): 7.15–7 (m, 5H); 6.93 (bd, 1H,
3
3
3J1H¼13.5 Hz); 4.62 (qd, 1H, J1H¼13.5 Hz, J3H
¼
9. (a) Otsuka, S.; Tani, K. Synthesis 1991, 9, 665–680. (b) Alper,
H.; Hachem, K. Trans. Met. Chem. 1981, 6, 219–220. (c) Tani,
K.; Yamagata, T.; Akutagawa, S.; Kumobayashi, H.;
Taketomi, T.; Takaya, H.; Miyashita, A.; Noyori, R.; Otsuka,
S. J. Am. Chem. Soc. 1984, 106, 5208–5217. (d) Inoue, S.;
Takaya, H.; Tani, K.; Otsuka, S.; Sato, T.; Noyori, R. J. Am.
Chem. Soc. 1990, 112, 4897–4905. (e) Otsuka, S.; Tani, K.
Asymmetric Synth. 1985, 5, 171–191. (f) Noyori, R. Chem.
Soc. Rev. 1989, 18, 187–208. (g) Tani, K.; Yamagata, T.;
Tatsuno, Y.; Yamagata, Y.; Tomita, K.; Akutagawa, S.;
Kumobayashi, H.; Otsuka, S. Angew. Chem. 1985, 97,
232–234. (h) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990,
23, 345–350. (i) Salas, M.; Al-Khawaja, I. K.; Thomas, M. J.;
Joule, J. A. J. Chem. Res. S 1988, 7, 218. (j) Stille, J. K.;
Becker, Y. J. Org. Chem. 1980, 45, 2139–2145. (k) Chiusoli,
G. P.; Costa, M.; Pivetti, F. J. Organomet. Chem. 1989, 373,
377–384.
3
6.7 Hz); 4.51 (s, 2H); 1.4 (bd, 3H, J1H¼6.7 Hz); 1.3 (s,
9H). 13C NMR (in C6D6 at 323 K, d, ppm): 153.29; 138.63;
128.8; 128.64; 126.95; 126.70; 103.79; 80.53; 48.08; 30.65;
28.22; 15.25. MS (ESI/TOF): 270 (100); 517 (23). IR: 2975;
2929; 1705; 1665; 1451; 1399; 1371; 1326; 1280; 1231;
1165.
4.2.10. 2-(2-Methyl-propenyl)-isoxazolidin-3-one. Not
1
separated from starting material. H NMR (d, ppm): 5.89
3
(bs, 1H); 4.4 (dd, 1H, J1H¼7.9 Hz, 9.2 Hz); 4.39 (dd, 1H,
3J1H¼6.8 Hz, 7.9 Hz); 3.79 (dd, 1H, 3J1H¼6.8 Hz, 9.2 Hz);
3
3.78 (t, 1H, J2H¼7.9 Hz); 1.8 (bs, 3H); 1.78 (bs, 3H).
Acknowledgements
10. Corriu, R.; Huynh, V.; Moreau, J.; Pataud-Sat, M.
J. Organomet. Chem. 1983, 255, 359–364.
We would like to thank Professor Crabtree (Yale university)
and Professor Krompiec (Silesian university) for helpful
discussions about the mechanism involved in this
isomerization.
11. Yamada, H.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1991,
56, 4569–4574.
12. Tatsumi, T.; Hashimoto, K.; Tominaga, H.; Mizuta, K.; Hata,
K.; Hidai, H.; Uchida, Y. J. Organomet. Chem. 1983, 252,
105–112.
13. (a) Onishi, M.; Oishi, S.; Sakaguchi, M.; Takaki, I.; Kiraki, K.
Bull. Chem. Soc. Jpn 1986, 59, 3925–3930. (b) Kumobayashi,
H.; Akutagawa, S.; Otsuka, S. J. Am. Chem. Soc. 1978, 100,
3949–3950.
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