Preparation and Characterisation of 2,2,2-Triphenyl-2λ 5 -1,3,2-Dioxastibolane-4,5-Dione as Standard For an Attempt to Trap 1,2-Dioxetanedione,A Possible High-Energy Intermediate in Peroxyoxalate Chemiluminescence †
Free accessOtherFirst published online September, 2002
Preparation and Characterisation of 2,2,2-Triphenyl-2λ 5 -1,3,2-Dioxastibolane-4,5-Dione as Standard For an Attempt to Trap 1,2-Dioxetanedione,A Possible High-Energy Intermediate in Peroxyoxalate Chemiluminescence †
The thermally stable triorganoantimony derivative, 2,2,2-triphenyl-2λ5-1,3,2-dioxastibolane-4,5-dione, has been prepared and characterised being then used as a reference in attempts to trap 1,2-dioxetanedione, one of the high-energy intermediates postulated in peroxyoxalate chemiluminescence, by an insertion reaction with triphenylantimony.
RauhutM.M., BollykyL. J., RobertsB. G., LoyM., WhitmanR. H., IannottaA. V., SemselA. M., and ClarkeR. A., J. Am. Chem. Soc., 1967, 89, 6515.
10.
CordesH.F., RichterH. P., and HellerC. A., J. Am. Chem. Soc., 1969, 91, 7209.
11.
DeCorpoJ.J., BaronavskiA., McdowellM. V., and SaafeldF. E., J. Am. Chem. Soc., 1972, 94, 2879.
12.
BaumstarkA.L., LandisM. E., and BrooksP., J. Org. Chem., 1979, 44, 4251.
13.
MatsumuraY., ShindoM., and OkawaraR., J. Organomet. Chem., 1971, 27, 357.
14.
MichaelisA., and ReeseA., Liebigs Ann. Chem., 1886, 233, 39.
15.
MirbachM., and WieberM., Gmelin Handbook of Inorganic Chemistry, 8th Ed., Sb, Organoantimony Compounds, Part 5, Springer-Verlag, Berlin, 1990, 38.
16.
RauhutM.M., Acc. Chem. Res., 1969, 2, 80; F. J. Alvarez, N. J. Parekh, B. Matuszewski, R. S. Givens, T. Higuchi and R. L. Schowen, J. Am. Chem. Soc., 1986, 108, 6435; M. Orlovic, R. L. Schowen, R. S. Givens, F. Alvarez, B. Matuszewski and N. Parekh, J. Org. Chem., 1989, 54, 3606; H. Neuvonen, J. Chem. Soc. Perkin Trans. 2, 1995, 945; H. Neuvonen, J. Chem. Soc. Perkin Trans. 2, 1995, 951; C. L. R. Catherall and T. F. Palmer, J. Chem. Soc. Faraday Trans. 2, 1984, 80, 823; C. L. R. Catherall and T. F. Palmer, J. Chem. Soc. Faraday Trans. 2, 1984, 80, 837.
17.
VenezkyD.L., SinkC. W., NevettB. A., and FortescueW. F., J. Organomet. Chem., 1972, 35, 131.
18.
We thank one of the referees for suggesting this possibility.
19.
ClarkeH.T., and DavisA. W., Org. Synth. Coll. vol. 1 (2nd Ed.), 1941, 421.
