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Hydrofunctionalisation of an Aromatic Triphosphabenzene
Author(s) -
Falconer Rosalyn L.,
Zeng Dihao,
Green Michael,
Stephan Douglas W.,
McGrady John E.,
Russell Christopher A.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903229
Subject(s) - diastereomer , silanes , substrate (aquarium) , chemistry , density functional theory , bicyclic molecule , aromaticity , computational chemistry , stereochemistry , medicinal chemistry , molecule , organic chemistry , oceanography , silane , geology
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.