CHED 866 |
| Guy Crundwell and Vanessa Stacy. Department of Chemistry, Central Connecticut State University, New Britain, CT 06050 |
| 2,2’-Thenoin and 3,3’-thenoin are symmetric thienyl-analogs of benzoin and were synthesized by the thiamine-catalyzed carboxaldehyde condensation reaction commonly found in undergraduate organic chemistry laboratory manuals. Oxidation to thenils was found to occur only by reaction with copper(II) acetate, HOAc, and ammonium nitrate whereas reactions of the thenoins with concentrated nitric acid did not yield acceptable product. The crystal structures of 2,2’- and 3,3’-thenils were determined via X-ray diffraction and the latter compound shows a ring flip commonly encountered in crystallized molecules with terminal thienyl rings. Syntheses of asymmetric thenil/benzils are underway. A direct co-condensation of benzaldehyde and 3-thiophenecarboxaldehyde yielded a mixed thenoin/benzoin which was oxidized to give 1-phenyl-2-(thien-3-yl)ethanedione. The crystal structure of this molecule is forthcoming. A direct co-condensation between benzaldehyde and 2-thiophenecarboxaldehyde was not as fruitful; therefore other routes to 1-phenyl-2-(thien-2-yl)ethanedione are being sought. Finally, the use of all thienyl-containing ethanediones as guests in crystals of benzyl is being examined. |
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Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Chemical Education |
