Tautomer-dependent Bergman cyclization of novel uracil-enediyne chimeras

Chang Sik Kim, Christian Diez, Keith C. Russell

Research output: Contribution to journalArticle

30 Scopus citations

Abstract

Uracil-enediyne chimeras 4, 7, and 8 were prepared and examined for their propensity to undergo Bergman cyclization. Kinetic experiments showed lactam tautomers 7 and 8 reacted up to 25 times faster than lactim ether 4. Determination of the activation energy for each cycloaromatization reaction, along with radical trapping agent dependent studies, indicate the rate differences result from different ground state energies of the starting enediynes.

Original languageEnglish (US)
Pages (from-to)1555-1558
Number of pages4
JournalChemistry - A European Journal
Volume6
Issue number9
DOIs
StatePublished - May 2 2000

Keywords

  • Cyclizations
  • Diradicals
  • Electrocyclic reactions
  • Enynes
  • Tautomerism

ASJC Scopus subject areas

  • Chemistry(all)

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