The retro Grignard addition reaction revisited: the reversible addition of benzyl reagents to ketones

Stig Holden Christensen, Torkil Holm, Robert Madsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

The Grignard addition reaction is known to be a reversible process with allylic reagents, but so far the reversibility has not been demonstrated with other alkylmagnesium halides. By using crossover experiments it has been established that the benzyl addition reaction is also a reversible transformation. The retro benzyl reaction was shown by the addition of benzylmagnesium chloride to di-tert-butyl ketone followed by exchange of both the benzyl and the ketone moiety with another substrate. Similar experiments were performed with phenylmagnesium bromide and tert-butylmagnesium chloride, but in these two cases the Grignard addition reaction did not show any sign of a reverse transformation.
Original languageEnglish
JournalTetrahedron
Volume70
Issue number7
Pages (from-to)1478-1483
ISSN0040-4020
DOIs
Publication statusPublished - 2014

Keywords

  • Crossover experiment
  • Grignard reagent
  • Nucleophilic addition
  • Reaction mechanism
  • Retro reaction

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