Origin of thermodynamic versus kinetic control of allene hydroboration with 9-borabicyclo[3.3.1]nonane and 10(R)-trimethylsilyl-9-borabicyclo[3.3.2]decane

Org Lett. 2009 Dec 3;11(23):5538-41. doi: 10.1021/ol902364d.

Abstract

Density functional theory was used to locate transition states for hydroboration reactions of allenes with 9-borabicyclo[3.3.1]nonane and 10-R-9-borabicyclo[3.3.2]decane, as well as transition states for [1,3]-boratropic shift and aldehyde addition reactions of the derived allylboranes. The origin of kinetic versus thermodynamic control in the allene hydroboration step is described.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemistry*
  • Alkanes / chemistry*
  • Boron Compounds / chemistry*
  • Kinetics
  • Molecular Structure
  • Thermodynamics

Substances

  • Alkadienes
  • Alkanes
  • Boron Compounds
  • propadiene
  • decane
  • nonane