3767
COMMUNICATIONS TO THE EDITOR
Oct. 5 , 1962 0
8
0
DDQ(II1a) B. sphaericus(I1Ib)
H," I'd
O
'
H
t
1113 - 0 11 1, -0 07
111 - - L O O *
2, t i n 1 in acetone 3 , Zn i i i IIAc
& & & B. sphaericus\IVb) DDQ(1Va)
0
~
0 IVa = O 24 =1.00 b =007 Va = 0 6 8 b =075 Numbers refer to the relative specific activities of reactants and products. 0
v
IV = l o o
*
from the mixture by paper chromatography, oxidized to the diketone using the Jones method9 and equilibrated with base to give V. Compound V was oxidized both with DDQ to give compound VA (68y0 retention of tritium) and with B. sphaericus to give compound VB (75% retention of tritium). The remaining tritium was shown t o be a t C-1 by oxidizing another sample of compound V to androsta-1,4,6-triene-3,17-dioneusing chloranil1° and then DDQ.6 When this compound was treated with acid it rearranged to 1-methylestrone acetate which was inactive (specific activity
