Reactivity of substituted 3-(diethylphosphonyl)-1-(trialkylsilyl)alka-1,3-dienes: Regioselective epoxidation and cyclopropanation reactions

Heteroatom Chemistry

Volumn 10, Issue 3, 1999, Pages 231-236

  Chevalier, Fabien ^a   Al Badri, Hashim ^a   Collignon, Noël ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0242592800     PISSN: 10427163     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-1071(1999)10:3<231::AID-HC9>3.0.CO;2-6     Document Type: Article

References (28)

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8. In a recent reinvestigation of the epoxidation mechanism of alkenes by peracids, the proposed oxygen transfer via a nonpolar concerted transition state confirms the standard Bartlett's mechanism. Angelis, Y. S.; Orfanopoulos, M. J Org Chem 1997, 62, 6083 and references cited therein.
9. Preliminary experiments showed the total lack of reactivity of the 3,4-double bond as well as of the 1,2-double bond of 1 toward the usual nucleophilic epoxidation reagent: alkaline hydrogen peroxide.
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16. Regioselective cyclopropanation of other electron-deficient conjugated dienes have recently attracted considerable interest in organic synthesis; see, for example, Löfström, C. M. G.; Ericsson, A. M.; Bourrinet, L.; Juntunen, S. K.; Bäckvall, J. E. J Org Chem 1995, 60, 3586 and references cited therein.
17. Shostakovsky, V. M.; Carlson, R. M. Synth Commun 1996, 26, 1785.
18. (a) The degree of diastereoselectivity of the cyclopropanation reaction of electron-deficient unsaturated substrates, using DMSY as reagent, seems to be very dependent on the nature of the substituents of the double bond;
19. see, for example, (b) Kaiser, C.; Trost, B. M.; Beeson, J.; Weinstock, J. J Org Chem 1965, 30, 3972; (c) Nozaki, H.; Itô, H.; Tunemoto, D.; Kondô, K. Tetrahedron 1966, 22, 441; (d) Landor, S. R.; Punja, N. J Chem Soc 1967, 2495; (e) Merz, A.; Märkl, G. Angew Chem Int Ed 1973, 12, 845.
20. see, for example, (b) Kaiser, C.; Trost, B. M.; Beeson, J.; Weinstock, J. J Org Chem 1965, 30, 3972; (c) Nozaki, H.; Itô, H.; Tunemoto, D.; Kondô, K. Tetrahedron 1966, 22, 441; (d) Landor, S. R.; Punja, N. J Chem Soc 1967, 2495; (e) Merz, A.; Märkl, G. Angew Chem Int Ed 1973, 12, 845.
21. see, for example, (b) Kaiser, C.; Trost, B. M.; Beeson, J.; Weinstock, J. J Org Chem 1965, 30, 3972; (c) Nozaki, H.; Itô, H.; Tunemoto, D.; Kondô, K. Tetrahedron 1966, 22, 441; (d) Landor, S. R.; Punja, N. J Chem Soc 1967, 2495; (e) Merz, A.; Märkl, G. Angew Chem Int Ed 1973, 12, 845.
22. see, for example, (b) Kaiser, C.; Trost, B. M.; Beeson, J.; Weinstock, J. J Org Chem 1965, 30, 3972; (c) Nozaki, H.; Itô, H.; Tunemoto, D.; Kondô, K. Tetrahedron 1966, 22, 441; (d) Landor, S. R.; Punja, N. J Chem Soc 1967, 2495; (e) Merz, A.; Märkl, G. Angew Chem Int Ed 1973, 12, 845.
23. Bentrude, W. G.; Setzer, W. N. In Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis; Verkade, J. G., Quin, L. D., Ed.; VCH: Deerfield Beach, FL, 1987; p 365.
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27. Maas G. Phosphorus and Sulfur 1983, 14, 143.
28. CP by electronegative α-substituents was in fact previously observed (see Ref. [21]).