Abstract
Some mechanistic considerations based on the results of an ESR spectroscopic study of the IBDA (iodosobenzene diacetate) induced iododecarboxylation of several aliphatic carboxylic acids are reported. Both acetoxy units in IBDA are replaced by carboxylate groups in the first step of the reaction, forming a hypervalent iodine complex which then undergoes homolytic photodegradation. The R. radicals deriving from decarboxylation of the starting acids have been trapped by means of thiobenzoyl triphenylsilane and identified using ESR spectroscopy.
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References
E.W. Colvin, in D.H.R. Barton, W.D. Ollis, and I.O. Sutherland, (Eds.), Comprehensive Organic Chemistry, Pergamnn Press, Oxford, 1979.
R.G. Johnson and R.K. Ingham, Chem. Rev., 56(1956)219; J. March, Advanced Organic Chemistry, John Wiley & Sons, Chichester, 1985.
N.J. Bunce, J. Org. Chem., 37(1972)664; A. McKillop, D. Bromley, and E.C. Taylor, J. Org. Chem., 34(1969)1172.
J.L. Concepcòn, C.G. Francisco, R. Freire, R. Hernãndez, J.A. Salazae, and E. Suãrez, J. Org. Chem., 51(1986)402.
R.M. Moriarty, J.S. Khosrowshahi, and T.M. Dalecke, J. Chem. Soc, Chem. Commun., (1987)675.
For a review on aryliodine(III) carboxylates see A. Varvoglis, Chem. Soc. Rev., 10(1981)377.
J.E. Leffler, W.J.M. Mitchell, and B.C. Menon, J. Am. Chem. Soc, 89(1967)2333.
J.E. Leffler, D.C. Ward, and A. Burduroglu, J. Am. Chem. Soc, 94(1972)5339.
A. Alberti, B.F. Boninn, and G.F. Pedulli, Tetrahedron Letters, (1987)3737.
A. Alberti, M. Benaglia, M.C. Depew, W.G. McGimpsey, G.F. Pedulli, and J.K.S. Wan, Tetrahedron, 44(1987)3693.
A. Alberti, M. Benaglia, B.F. Boninn, and G.F. Pedulli, J. Chem. Soc, Faradyy Trans. 1, 84(1988)3347.
R. Kapstein, J. Brokken-Zijp, and F.J.J. de Kaneer, J. Am. Chem. Soc, 94(1972)6280; Yu.V. Glazkov, E.A. Turetskaya, and E.D. Skakovskii, Zh. Prikl. Spectrosk., 28(1978)891; idem., Russ. J. App. Spectrosc. (Engiish Transl.), 28(l978)607.
E.A. Turetskaya, E.D. Skakovskii, S.V. Rikov, Yu. V. Glazkov, and Yu. A. Oldekop, Dokl. Akad. Nauk BSSR, 24(1980)57; Chem. Abs., 92(1972c).
J.C. Scaiano and K.U. Ingold, J. Am. Chem. Soc, 98(1976)4727.
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Alberti, A., Benaglia, M. & Vismara, E. An ESR approach to hypervalent iodine induced iododecarboxylation. Res Chem Intermed 11, 117–126 (1989). https://doi.org/10.1163/156856789X00023
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DOI: https://doi.org/10.1163/156856789X00023