PERIODATE–PERMANGANATE OXIDATIONS: I. OXIDATION OF OLEFINS

Canadian Science Publishing - Tập 33 Số 11 - Trang 1701-1709 - 1955
René Lemieux, E. von Rudloff

Tóm tắt

It was discovered that olefinic double bonds are readily oxidized in an aqueous solution of periodate which contains only catalytic amounts of permanganate. The data suggest that in the effective pH range of 7 to 10 the permanganate is not reduced at once beyond the manganate state and that it is regenerated from this state by periodate action. Evidence was obtained that the main course of the oxidation of an olefin of type —CH=CH— involves first permanganate oxidation to hydroxyketones which are then rapidly cleaved by periodate to products which may subsequently be oxidized by the permanganate.

Từ khóa


Tài liệu tham khảo

BUIST G. J., 1954, J. Chem. Soc. 1406.

DRUYMOND A. Y., 1953, J. Chem. Soc. 435.

KING G, 1936, J. Chem. Soc. 1788.

LAPWORTH A., 1925, J. Chem. Soc. 1628.

LEMIEUX R. U., 1954, Chem., 26, 920

LEYIEUX R. U., 1955, J. Chem., 33, 1710

PATARI, 1944, Seifen., 51, 347, 10.1002/lipi.19440510903

H, 1938, J. Am. Chem. Soc., 60, 2726, 10.1021/ja01278a053

RUBY C. E, 1921, J. Am. Chem. Soc., 43, 294, 10.1021/ja01435a006

RUDLOFP E, 1955, VON. Can. J. Chem., 33, 1714, 10.1139/v55-210

SWERN D., 1945, J. Am. Chem. Soc., 67, 1786, 10.1021/ja01226a050

WATERS W. A., 1946, Faraday Soc., 42, 184, 10.1039/tf9464200184