Rearrangements of trihalomethyl ketones

Samuel Braverman, Marina Cherkinsky, E. V.K.Suresh Kumar, Hugo E. Gottlieb

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Trihalomethyl ketones have been prepared and their reactivity under basic conditions was investigated in terms of competition between 1,2- vs. 1,3-elimination and nucleophilic substitution. Favorskii rearrangement was the preferred process, but in those cases where electronic or steric effects were present, nucleophilic substitution became dominant. No evidence of ketene formation was detected. The mechanism of formation of the various rearrangement products is discussed. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)4521-4529
Number of pages9
JournalTetrahedron
Volume56
Issue number26
DOIs
StatePublished - 23 Jun 2000

Bibliographical note

Funding Information:
The financial support of this study by the National Science Foundation is gratefully acknowledged. One of us (E. V. K. S. K.) is also indebted to the Vatat Committee for a postdoctoral fellowship.

Keywords

  • Favorskii rearrangement
  • Ketone
  • γ-elimination

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