Diastereoselective synthesis and molecular structure of a bicyclic and a cage phosphane

Chemische Berichte

Volumn 130, Issue 10, 1997, Pages 1547-1550

  Bekiaris, Gcorgios ^a   Lork, Enno ^a   Offermann, Werner ^a   Röschenthaler, Gerd Volker ^a  

^a UNIVERSITY OF BREMEN   (Germany)

Author keywords

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Indexed keywords

EID: 0141597483     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19971301031     Document Type: Article

References (25)

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3. A. B. Bruker, E. I. Grinshtein, L. Z. Soborovski, Zh. Obshch. Khim. 1966,36, 1138-1141 (Chem. Abstr. 1966,65, 12230h)
4. R. Francke, G.-V. Röschenthaler, Chem.-Ztg. 1989, 113, 320-321
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11. F. Seifert, G.-V. Röschenthaler, Z. Nawrforsch., B: Chem. Sei. 1993,48, 1089-1093
12. R. Francke, G.-V. Röschenthaler, Chem.-Ztg. 1989, 113, 183-186
13. E.g.: l,l,l-Tnfluoro-2-hydroxypentan-4-one shows no significant tautomerism, c.f.: A. Forni, I. Moretti, F. Prati, G. forre, Tetrahedron 1994,50, 11995-12000
14. Similar intramolecular hydrogen bonding is discussed in 1,1,1trifluoro-2-hydroxy-4-alkanones, c.f.: E. Kiehlmann, B. C. Menon, N. McGillivray, Can. J. Chem. 1973, 57, 3177-3181
15. O. Casher, D. O'Haaan, C. A. Rosenkranz, H. S. Rzepa, N. A. Zaidi, J. Chem. Soc, Chem. Commun. 1993, 1337-1340
16. F. A. Carey, R. J. Sundberg, Organische Chemie, VCH, 1995, pp. 140-146;
17. A. J. Kirby, The Anomeric Effect and Related Stercoelectronic Effects at Oxygen, Springer, Berlin, 1983
18. The phosphadamantane chair-chair precursor (analogue of 6b) was not obtained, since the hydrogen bond of the 4-OH group (with CF3, CH2, and PH substituents) is probably less pronounced than in the case of the 6-OH group (with CF3, CH2, and oxygen substituents) directing the hemiketal formation as described above; c.f. hydrocen-bonding properties of CF3CH,OH: A. D. Sherry, K. FTPurcell, J. Phys.Chem. 1970, 74, 3535-3543;
19. I. A. Koppel, V. A. Eiber, U. H. Mölder, Org. React. 1984, 27, 40-58. The formation of water is unfavorable, too, and not observed under the reaction conditions applied, because of the strong C-O(H) bond at the trifluoromethylated carbon atoms present
20. J. B. Hendrickson, J. Am. Chem. Soc. 1967, 59, 7036-7043
21. Phosphorinane has an axial P-H bond in a chair conformation in solution, cf.: J. B. Lambert, W. L. Oliver, Tetrahedron 1971, 27, 4245
22. P. D. Cradwick, G. A. Sim, J. Chem. Soc. B, 1971, 2218-2221
23. The 5p ('./PH) values are in the expected region (of the expected order); see: S. Berger, S. Braun, H.-O. Kalinowski, NMR-Spekroskopie von Nichtmetallen: 3lP-NMR-Spekroskopie, Thieme, Stuttgart, 1993, p. 6, p. 126
24. Possibly the (Z) isomer was formed. A signal at 5P = -120.4 (tdq, './p, = 209.0, VPH = 17.6 Hz, VPF = 3.5 Hz) can be attributed to the (E) isomer
25. Further details of the crystal structure investigations are available from the Fachinformationsdienst Karlsruhe, D-76344 Egeenstein-LeopoIdshafen (Germany), on quoting the depository numbers CSD-406880 (6a) and -406881 (7).