One-Pot Synthesis of Cage-Functionalized,Ketal-Containing Crown Ethers |
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| Authors: | Watson William H Bodige Satish G Marchand Alan P Chong Hyun-Soon |
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| Institution: | (1) Department of Chemistry, Texas Christian University, P.O. Box 298860, Fort Worth, Texas, 76129-8860;(2) Department of Chemistry, Texas Christian University, P.O. Box 298860, Fort Worth, Texas, 76129-8860;(3) Department of Chemistry, University of North Texas, NT Station, Box 305070, Denton, Texas, 76203-5070;(4) Department of Chemistry, University of North Texas, NT Station, Box 305070, Denton, Texas, 76203-5070 |
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| Abstract: | Acid-catalyzed reaction of pentacyclo5.4.0.02,6.03,10.05.9]undecane-8,11-dione (1) with penta(ethylene glycol) produced two cage-functionalized, ketal-containing crown ethers, i.e., 2 and 3, in low yield. The structure of 2 was established unequivocally by direct methods. Alkali metal picrate extraction data obtained for 2 and for a structurally related model compound, i.e., 18-crown-6,indicate that 2 is an inefficient alkali metal picrate extracting agent. |
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| Keywords: | Crown ethers X-ray structure molecular mechanics calculations alkali metal picrate extraction host– guest chemistry |
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