Abstract
The comparative oxidation of trans-hex-2-enol to leaf aldehyde has been effected with the aid of manganese dioxide, chromium oxide, and sodium dichromate in DMSO. It has been established that sodium dichromate in DMSO gives the best yield (not less than 80%) and a product of higher purity. It is a comparatively new reagent in organic synthesis. The use of sodium dichromate in DMSO is promising in the preparation of compounds requiring the use of mild conditions.
Similar content being viewed by others
Literature cited
A. Hatanaka, Kagaku (Kyoto),30, 347 (1975).
A. Hatanaka, Koryo, No. 101, 29 (1972).
T. Curtius and H. Franzen, Ann. Chem.,390, 89 (1912).
S. Seck and J. Crauzet, Phytochemistry,12, 2925 (1973).
R. A. Flatch, R. K. Forrey, and D. G. Guadagni, J. Agric. Food Chem.,21, 948 (1973).
S. Kamiyama, Agric. Biol. Chem.,34, 540 (1970).
A. Hatanaka and T. Harada, Phytochemistry,12, 234 (1973).
E. D. Lund, R. E. Berry, C. J. Wagner, and M. K. Veldhuis, J. Agric. Food Chem.,20, 685 (1972).
Y. Naya and M. Kataka, Bull. Chem. Soc., Jpn.,44, 3116 (1971).
H. E. Nursten and A. A. Williams, J. Sci. Food Agric.,20, 613 (1969).
J. T. Baker and P. A. Jones, Austr. J. Chem.,22, 11793 (1969).
A. I. Virtanen and C. G. Spare, Suom. Kemistil.,34-B, 18 (1961).
L. M. Roth, W. D. Niegish, and W. H. Stahl, Science,123, 670 (1956).
O. W. L. Bevan, A. J. Brich, and H. Caswell, J. Chem. Soc., 488 (1961).
A. Hatanaka, O. Adachi, and M. Okuyama, Agric. Biol. Chem.,34, 1574 (1970).
K. Saigo, A. Morikawa, and T. Mukaiyama, Bull. Chem. Soc., Jpn.,49, 1656 (1976).
A. Hatanaka, Bull. Inst. Chem. Res. Kyoto Univ.,50, 192 (1972).
A. Hatanaka and M. Ohno, Agric. Biol. Chem.,35, 1044 (1971).
French Patent No. 2,098,809 of March 10, 1972.
M. Ohno and A. Matanaka, Bull. Inst. Chem. Res. Kyoto Univ.,40, 322 (1962).
Y. S. Rao and R. Filler, J. Org. Chem.,39, 3304 (1974).
M. S. Newman, J. Am. Chem. Soc.,71, 1292 (1949).
K. N. Campbell and L. T. Eby, J. Am. Chem. Soc.,63, 216 (1941).
J. Attenborrow, J. Chem. Soc., 1094 (1952).
Additional information
Tartu State University. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 298–300, May–June, 1977.