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.
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.
Ess
Daniel H
DH
Department of Chemistry, The Scripps Research Institute, Jupiter, Florida 33458, USA. daniel@scripps.edu
Kister
Jeremy
J
Chen
Ming
M
Roush
William R
WR
D000466:Alkadienes / Q000737:chemistry*; D000473:Alkanes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D013816:Thermodynamics
D000466:Alkadienes; D000473:Alkanes; D001896:Boron Compounds; C025947:propadiene; C012867:decane; C017573:nonane