Steric control of geminal Lewis pair behavior: Frustration induced dyotropic rearrangement

Éva Dorkó, Eszter Varga, Tamás Gáti, Tamás Holczbauer, Imre Pápai, Hasan Mehdi, Tibor Soós

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

A series of methylene-linked boron/nitrogen geminal Lewis pairs were synthesized and the impacts of sterical effect on their chemical behavior were systematically investigated. Increasing the steric demand around the boron atom is manifested first by an incremental change in the structure of the resulting dative adducts. Accordingly, in the case of phenyl substituents (Alk 2NCH2BPh2), formation of head-to-tail dimers/oligomers was observed, while such an intermolecular association was avoided when o-tolyl moiety was introduced [Alk2NCH 2B(o-Tol)2], affording only an intramolecular dative complex. Further increase of sterical hindrance to a point (i.e. using mesityl substituents), however, caused a radical change in the structure; a dyotropic rearrangement occurred. Thus, steric interference induced a rearrangement in the geminal pair to relieve or minimize the frustration strain.

Original languageEnglish
Article numberst-2014-b0238-c
Pages (from-to)1525-1528
Number of pages4
JournalSynlett
Volume25
Issue number11
DOIs
Publication statusPublished - Jul 2014

Keywords

  • Lewis acids
  • boron
  • dyotropic rearrangement
  • frustrated Lewis pairs
  • steric hindrance

ASJC Scopus subject areas

  • Organic Chemistry

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