First characterisation of enol carbonate and enol carbamate radical cations in solution. Kinetics and selectivity of the mesolytic cleavage of the O-CO bond

Chemistry Letters

Volumn , Issue 4, 1997, Pages 299-300

  Schmittel, Michael ^a   Trenkle, Holger ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031515803     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.299     Document Type: Article

References (31)

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14. The model compounds could be easily prepared by reaction of the corresponding enolates with the appropriate acyl derivatives and have been fully characterised.
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21. Fc.
22. The butylaminoacyl radical adopts the conformation from the parent enol and does not convert into the (E)-form during the EPR experiment: R. Sutcliffe and K. U. Ingold, J. Am. Chem. Soc., 103, 7686 (1981).
23. The EPR signals of the benzofuran radical cations including the hyperfine splittings are known from independent studies. M. Schmittel, G. Gescheidt, L. Eberson, and H. Trenkle, J. Chem. Soc., Perkin Trans. 2, submitted.
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28. The same trend is seen in acetonitrile, but it is not possible to quantify the effect since the observed rate constants represent only an upper limit for the mesolytic cleavage because of disproportionation reactions.
29. D. D. M. Wayner and V. D. Parker, Acc. Chem. Res., 26, 287 (1993).
30. Based on the AM1 calculated homolytic bond energies.
31. M. Röck and M. Schmittel, J. Chem. Soc., Chem. Commun., 1993, 1739.