REACTIONS OF CYCLIC OXALYL COMPOUNDS .34. SYNTHESIS OF DIBENZOYLACETATE-N-CARBOXYALKYLAMIDES AND SEMIEMPIRICAL CALCULATIONS OF KETO-ENOL TAUTOMERS


FABIAN W., KOLLENZ G., AKCAMUR Y., KOK T., TECZAN M., AKKURT M. , ...More

MONATSHEFTE FUR CHEMIE, vol.123, no.3, pp.265-275, 1992 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 123 Issue: 3
  • Publication Date: 1992
  • Doi Number: 10.1007/bf00810475
  • Title of Journal : MONATSHEFTE FUR CHEMIE
  • Page Numbers: pp.265-275

Abstract

4-Benzoyl-5-phenylfuran-2,3-dione (1) and the urethanes 2 combine under loss of carbon monoxide yielding the open chain dibenzoylacetic acid derivatives 3 and 4. 3a, b only can be cyclized to the oxazinone 5. The keto-enole tautomerism 3 half arrow right over half arrow left 4 is further investigated with aid of semiempirical quantum chemical calculations, based upon the molecular geometry of 3a, deduced from an X-ray study.