Pseudo first-order rate constants are determined for the oxidation of a series of secondary alcohols and their monodeutero analogues by ammonium chromate in aqueous acidic solution at several temperatures; the relative rates and activation parameters are consistent with a cyclic, symmetrical transition state.
References
1.
StewartR., Oxidation Mechanisms, W. A. Benjamin, New York, 1964, pp. 33–48.
2.
WibergK. B., Oxidation in Organic Chemistry, Part A, ed. WibergK. B., Academic Press, New York, 1965, pp. 142–170.
3.
LeeD. G., Oxidation, ed. AugustineR. L., Marcel Dekker, New York, 1969, pp. 56–63.
4.
HudlickýM., Oxidation in Organic Chemistry, American Chemical Society, Washington, 1990, pp. 133–138.
5.
WestheimerF. H., and NicolaidesN., J. Am. Chem. Soc., 1949, 71, 25; M. Cohen and F. H. Westheimer, J. Am. Chem. Soc., 1952, 74, 4387.
6.
KwartH., and FrancisP. S., J. Am. Chem. Soc., 1959, 81, 2116.
7.
MüllerP., and PerlbergerJ.-C., Helv. Chim. Acta, 1974, 57, 1943; J. Am. Chem. Soc., 1975, 97, 6862; 1976, 98, 8407; P. Müller, Chimia, 1977, 31, 209.
8.
NagarajanK., SundaramS., and VenkatasubramanianN., Indian J. Chem., Sect. A, 1979, 18, 260; J.-C. Richer and N. T. T. Hoa, Can. J. Chem., 1969, 47, 2479.
9.
Eckert-MaksićM., TušekL., and SunkoD. E., Croat. Chem. Acta, 1971, 43, 79.
10.
KakisF. J., FetizonM., DouchkineN., GolfierM., MourgesP., and PrangeT., J. Org. Chem., 1974, 39, 523.
11.
BrownH. C., KimS. C., and KrishnamurthyS., J. Org. Chem., 1980, 45, 1.
12.
NongkynrihI., and MahantiM. K., Bull. Chem. Soc. Jpn., 1996, 69, 1403.
13.
ÖzgünH. B., DeğirmenbasiN., J. Chem. Res. (S), 1997, 32.