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The Quest for Twofold Reductive P–C Bond Cleavage of P– Ph Substituted 1,4‐Dihydro‐1,4‐diphosphinine Derivatives
Author(s) -
Koner Abhishek,
Kunz Michael,
Schnakenburg Gregor,
Streubel Rainer
Publication year - 2018
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201800753
Subject(s) - chemistry , tricyclic , medicinal chemistry , iodide , imidazole , cleavage (geology) , stereochemistry , organic chemistry , geotechnical engineering , fracture (geology) , engineering
It is demonstrated that backbone chloro(phenyl)phosphanyl‐substituted imidazole‐2‐thiones 3 ( N‐ R = Me, Et, n Bu) can be easily synthesized which allow for a selective access to tricyclic 1,4‐diphenyl‐1,4‐dihydro‐1,4‐diphosphinines 5 via reaction with LDA. Furthermore, new examples for preferred substitution reactions are provided that occurred when KHMDS was used thus yielding P– N(SiMe 3 ) 2 substituted derivatives 4 . The new P– Ph substituted tricyclic 1,4‐dihydro‐1,4‐diphosphinine derivatives 5 were successfully employed to generate tricyclic bis‐phosphanides 6 using potassium in THF, and the formation of 6 was proven via quenching with excess of n ‐butyl iodide to give P–n Bu substituted derivatives 7 obtained as mixture of cis and trans isomers.