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Hydrofunctionalisation of an Aromatic Triphosphabenzene
Authors:Dr. Rosalyn L. Falconer  Dihao Zeng  Prof. Michael Green  Prof. Douglas W. Stephan  Prof. John E. McGrady  Dr. Christopher A. Russell
Affiliation:1. School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS UK;2. Department of Chemistry, University of Oxford, South Parks Road, Oxford, OX1 3QZ UK;3. Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada
Abstract:The aromatic heterocycle 2,4,6-tri-tert-butyl-1,3,5-triphosphabenzene reacts with a series of silanes, germanes and stannanes, with weaker E−H bonds reacting in an increasingly facile manner. All react by 1,4-addition to give bicyclic products with diastereomeric ratios varying with the substrate. Density functional theory (DFT) calculations show that activation of the E−H bond occurs across the 1,4-C/P axis of the triphosphabenzene, with the small energetic differences with respect to the stereochemistry of the addition offering insight into the experimentally observed diastereomeric ratios.
Keywords:hydrofunctionalisation  hydrosilylation  metal-free synthesis  phosphorus  triphosphabenzene
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