Lewis Acid Promoted Decomposition of Substituted L,3,2λ5-Dioxaphospholanes: Kinetic and Thermodynamic Studies

Journal of Organic Chemistry

Volumn 54, Issue 10, 1989, Pages 2440-2446

  Murray, William T ^a   Evans, Slayton A ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009328147     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00271a039     Document Type: Article

References (27)

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10. Murray, W. T.; Evans, S. A., Jr. Nouv J. Chem., in press.
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12. Baumstark and co-workers have presented kinetic evidence that supports the generation of betaine intermediates during the thermal decomposition of l,3,2λ5-dioxaphospholanes. See: Baumstark, A. L.; McClosky, C. J.; Williams, T. E.; Chisope, D. R. J. Org. Chem. 1980, 45, 3593–3597.
13. Luckenbach, R. Dynamic Stereochemistry of Pentaco-ordinated Phosphorus and Related Elements; George Thieme Verlag: Stuttgart, 1973.
14. The 31P NMR shifts reported here are consistent to those reported for analogous oxyphosphonium salts. For example (a) ethoxy-triphenylphosphonium tetrafluoroborate (31P 6 62.0 ppm), see; Denney, D. B.; Denney, D. Z.; Wilson, L. A. Tetrahedron Lett. 1968, 85–9. (b) (Neopentyloxy)triphenylphosphonium bromide (31P δ 61.7 ppm), see: ref 5. (c) Varasi, M.; Walker, K. A. M.; Maddox, M. L. J. Org. Chem. 1987, 52, 4235.
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19. The ability for anionic complexation to phosphorus has been proposed for the interaction of LiX (X = Cl, Br, I.,C104with the sterically less hindered 2-methyl-2-oxo-4-methylL,3,2λs-dioxaphosphol-4-ene. See: van Lier, J. J. C.; van de Ven, L. J. M.; de Haan, J. W.; Buck, H. M. J. Phys. Chem. 1983. 87. 3501.
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