1191
NOTES
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the acidities of the respective carboxylic acids,s Acknowledgment.-We wish to thank the Reand probably also by the comparison of the rates search Corporation for financial support of this of the alkaline hydrolysis of the carboxylic esters.9 work. It is noteworthy that the principal absorption DEPARTMEST OF CHEMISTRY bands of the four chalcone analogs, in which the 2- DUQUESNE UNIVERSITY PITTSBURGH 19, PENNA. thienyl and 2-fury1 groups replace both of the phenyl groups, are located within a verv narrow range. This would seem to imply the absence of A Preparation of Progesterone-4-CI4 any special resonance contributions by the 2 thienyl group in which the sulfur atom has an B Y L. M . THOMPSON, C. H. YATEBA N D A. D. ODEI,L expanded valence shell. RECEIVED SEPTEMBER 18, 1953 Experimental All of the heterocyclic chalcone analogs were prepared according to the directions of tveygand and Strobelt.Io The absorption spectra were determined i n 95% ethanol using a Beckman DU spectrophotometer. The spectral characteristics of the compounds discussed here are summarized in Table I, and the absorption curves of all of the compounds are reproduced in Figs. 1 and 2 .
3.0
This investigation was undertaken to fulfill the need for substantial quantities of ring-labeled progesterone-C14required as a starting material for biological and chemical conversion to radioactive corticosteroids.' By including radiocarbon in the 4position of the steroid nucleus, it was hoped that the label would persist in the metabolic fragments as indicated by studies conducted with cholesterol-lel"."
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Three procedures have been published concerning the inclusion of radiocarbon in the a,p-unsaturated ; .Kalamazoo, , &rich,,and returned to us for completion of the synthesis of curtisune acetate by known methods; c i . 1'. H . Kritchevsky, D. I,. Garmaise and T . P. Gallagher, THIS J O U R N A L , 7 4 , 183 ( I R 5 2 ) . 12) I . I,. Chaikaff, hl. D. Siperstein, W . G. Dauben, H. I,. Bradlow. J. F. Eastham, G . RI. Tomkins, J . R . Ileier. R . W . Chen, S Hotta and P. A . Srere, J . Bioi. C h e m . , 194, 413 (1952). (3) R B. Turner, THISJ O U R N A L 7 2, , 378 11950). (1) J , Ashmore. W. H. Elliott, E . A , Dois!, Jr., and E. A I k J i S Y . J . B i d . Cketn . 200, 661 (1963). in) hf. G u t , Helv. Chim. A c l a , 36, 906 (19.53). (6) R. D. H. Heard and P. Ziegler, THIS J O U R N A L T 2. , 4328 ( l Q 5 0 ) . 17) B. Belleau, Thesis, SlcGill University, 1950 18) (a) G. I . Fujimoto, THISJ O U R N A L . 73, 1856 ( I n s l ) , ( h ) C, I . Fujimoto and J . Prager, ibid., 7 6 , 3259 (1953). ( ! I ) R. D . H. Heard and P. Ziegler, i b i d . , 73,4036 (19c51). (10) A. I, Wilds and C. H . Shunk, i b i L , 7 0 , 2427 (1948). I I I ) T Reichstein and H. G. Fuchs. Hrlr,. Chiin. ALL I , 8 3 , 676 f1!)101. , 12, 1. R Jxniimon, unl~uhli
