By Robert P. Cook

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1956 ). Exceptions to this rule are C-3 and C-7 ketones. 5. Reactions of Double Bonds in Steroids The two angular methyl groups effectively prevent approach by a reagent to the front (ß face) of the steroid nucleus at those double bonds in their immediate vicinity (1, 2, 3, 9 ( 1 1 ) , 1 1 ) . Thus attack by peracids gives 1α,2α; 2α,3α; 9α,11α; and 11α,12α epoxides almost exclusively. Hindrance is not so marked with double bonds in the 4 and 5 positions. Thus cholesterol gives with peracids a mixture of a- and βepoxides; with cholesteryl esters the proportion of α-oxide is increased, possible due to the extra hindrance of the ester grouping.

The molecular rotation of cholesterol [M] is given at various wavelengths from 300 to 650 τημ by: [Μ] = _ 4 8 . , 1955c). Cholesterol purified either by acetic acid crystallization or via the dibromide gives no color in the selenium dioxide test of Fieser (1953a) 7 (absence of A -cholestenol, e t c ) . The constants quoted above refer to anhydrous cholesterol which is obtained by crystallization from dry solvents. It then forms triclinic needles. From moist solvents, it separates as the monohydrate, rhombshaped triclinic plates, which lose water at 70-80° C.

Rosenkranz et al, back and Reichstein, 1944). 1950a, 1950b). (gg) Se0 2-ferf BuOH-AcOH (Meystre ( p. q ) Collidine rx. ( Butenandt et al, et al, 1956; cf. Ringold et al, 1956; 1939). Szpilfogel et al, 1956). This reaction ( r ) NBS-CCl 4-Bz 20 2 in strong light. has not been reported in the choles(s) Collidine rx. (Romo et al, 1950a). terol series. (t) A c 2 0 - H 2 S 0 4 (Inhoffen and Zühls(7i/i) KOAc-AcOH at 200° (Butenandt dorf, 1941); Woodward et al, 1953). and Wolff, 1935). NOTE: In ( X X I I ) , there should be a double bond between C-6 and C-7; in ( X X V ) , there should be a single bond between C-8 and C-9.

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