Experimental support for planar pseudopericyclic transition states in thermal cheletropic decarbonylations

Han Xun Wei, Chun Zhou, Sihyun Ham, Jonathan M. White, David M. Birney

Research output: Contribution to journalArticlepeer-review

47 Scopus citations

Abstract

(Chemical Equation Presented) Low-temperature crystal structures of three pyrrolediones (3-5) and a furandione (9) were obtained and compared to structurally related compounds that cannot undergo decarbonylation. Systematic trends in bond lengths and angles are consistent with distortions along the reaction coordinate, in accord with the structure correlation principle of Dunitz. Since the pyrroledione and furandione rings in 3-5 and 9 are planar, these ground-state geometries prefigure the calculated planar, pseudopericyclic transition states.

Original languageEnglish
Pages (from-to)4289-4292
Number of pages4
JournalOrganic Letters
Volume6
Issue number23
DOIs
StatePublished - Nov 11 2004

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