NMR study of the sigmatropic [1,3]-B shift in 7,8-dipropyl-7-borabicyclo[4.2.2]deca-2,4,9-triene

I. D. Gridnev, M. E. Gurskii, A. O. Krusavin, Yu N. Bubnov

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1 Citation (Scopus)

Abstract

Activation parameters of the interconversion of geometric isomers 6a and 6b were determined by a complete lineshape analysis of the temperature-dependent 13C NMR spectra of 7,8-dipropyl-7-borabicyclo[4.2.2]deca-2,4,9-triene (6). For the reaction 6a → 6b, ΔG*298 = 52.2±0.1 kJ mol-1, ΔH* = 27.9±0.5 kJ mol-1, ΔS* = -82±8 J mol-1 K-1; For the reaction 6b → 6a, ΔG*298 = 52.6±0.1 kJ mol-1, ΔH* = 24.7±0.5 kJ mol-1, ΔS* = -93±10 J mol-1 K-1. The interconversion of deuteropyridine complexes 9a and 9b proceeds via their dissociation, which indicates that the rearrangement of borane 6 occurs according to the [1,3]-B shift mechanism.

Original languageEnglish
Pages (from-to)2127-2135
Number of pages9
JournalRussian Chemical Bulletin
Volume45
Issue number9
DOIs
Publication statusPublished - 1996 Sep
Externally publishedYes

Keywords

  • Activation parameters
  • Allylboranes, [1,3]-B shift
  • Dynamic NMR

ASJC Scopus subject areas

  • Chemistry(all)

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