An easy access to symmetrical Z-olefins from phosphorus ylides

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7703-7706

  Poulain, S ^a   Noiret, N ^a   Patin, H ^a  

^a UNIV RENNES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030597150     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01737-6     Document Type: Article

References (19)

1. 1. Bestmann, H.J.; Kratzer, O. Chem. Rev. 1963, 96, 1899-1908.
2. 2. a) Bestmann, H.J.; Armsen, R.; Wagner, H. Chem. Ber. 1969, 102, 2259-2269.
3. b) Rihter, B.; Masnovi, J. J. Chem. Soc., Chem. Commun., 1988, 35-37.
4. c) Nürrenbach, A.; Paust, J.; Pommer, H.; Schneider, J.; Schulz, B. Liebigs Ann. Chem., 1977, 1146-1159.
5. d) Bestmann, H. J.; Kisielowski, L.; Distler, W. Angew. Chem. Int. Ed. Engl., 1976, 15, 298-299.
6. e) Nürrenbach, A.; Pommer, H. Liebigs Ann. Chem., 1969, 721, 34-42.
7. f) Davis, F.A.; Chen, B-C. J. Org. Chem. 1990, 55, 360-363.
8. 3. a) Bestmann, H.J.; Häberlein, H.; Wagner, H.; Kratzer, O. Chem. Ber. 1966, 99, 2848-2854.
9. b) Bestmann, H.J.; Pfüller, H. Angew. Chem. Int. Ed. Engl. 1972, 11, 508-509.
10. 4. a) Schlosser, M; Christmann, K.F. Justus Liebig Ann. Chem. 1967, 708,1.
11. b) Schlosser, M Angew. Chem. Int. Ed. Engl., 1968, 7, 650.
12. c) Schlosser, M; Schaub, B. J. Am. Chem. Soc. 1982, 104, 5821-5823.
13. d) Reitz, A.B.; Mutter, M. S.; Maryanoff, B.E. J. Am. Chem. Soc. 1984, 106, 1873-1875.
14. 4) and chromatographed on silica gel to afford pure symmetrical olefins (procedure A). In case of less soluble phosphonium salts (2f-g), a mixture of dry THF and N, N′ - dimethylpropyleneurea (DMPU) was conveniently used (procedure B).
15. 6. Frost, D.J.; Gunstone, F.D., Chem. Phys. Lipids 1975, 15, 53-85.
16. 7. Gunstone, F.D.; Pollard, MR.; Scrimgeour, CM.; Vedanayagam, H.S. Chem. Phys. Lipids 1977, 18, 115-129.
17. 8. At least 2 runs for each condition have been performed. For each run, the (Z/E) ratio was determined by gas chromatography (3 injections per run on two columns of different polarity (column BP1 (SGE) and SP-2380 (SUPELCO)). Retention times were compared to those of authentical samples.
18. 9. Schlosser, M.; Schaub, B.; de Oliveira-Neto, J.; Jeganathan, S. Chimia 1986, 40, 244-245.
19. 10. Three different samples of sodium amide were used for two different runs, in each case.