there was added 100 mg. of sodium iodide arid the mixture \vas refluxed in a nitrogen atmosphere for 6 hr. The usual working up7* afforded 70 mg. of a brownish oil which crystallized froin ether-hexane. The product was filtered over 10 g. of alumiriuni oxide (activity 11-111) affording 42 mg. (8671 yield) of ll-dcb ~ 1164-168", g ~ 2 ~ identified h y :i hydroprogesterone ( \ ' I I I ) , ~ ~ 1 11n.p. mixture melting point with an authentic sample arid l)y thr coiiiparison of its infrared spectrum with that of authentic material. Negative Attempts of Isomerization of llp,l2~~Dibromoprogesterone (VII). (a)-A quantity of 50 mg. of llp,12~~-dibronioprogesterone (VIIj wits subjected for 30 min. to fusion, accordiiig to the procedure of Barton and King.Z1 Chromatography o i i silica gel of the resulting product afforded 18 mg. of a crystalline material, 1n.p. 98-103"; [ c Y ] * ~ D+98" ( c , 1.000 in CHCl:{'I, colitaining only little bromine (4.85c): :::P Y450 c m - l ( w r > -l>roatl. associated hydroxy band), 171
