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Synthesis of 1,3‐Diphospha‐2,3‐dihydro‐1 H ‐phenalenes
Author(s) -
Tarasevych Arkadii,
Shevchenko Igor,
Rozhenko Alexander B.,
Röschenthaler GerdVolker
Publication year - 2010
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.200901033
Subject(s) - chemistry , borane , medicinal chemistry , nuclear magnetic resonance spectroscopy , chlorine atom , cis–trans isomerism , chlorine , spectroscopy , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics
Abstract The reaction of 1,8‐dilithionaphthalene ( 1 ) with methylenebis[(dialkylamino)chlorophosphanes] [R 2 N(Cl)PCH 2 P(Cl)NR 2 ; R = Me ( 2a ), Et ( 2b )] leads to the formation of new heterocyclic compounds, 1,3‐diphospha‐2,3‐dihydro‐1 H ‐phenalenes 3a , b as a mixture of cis and trans isomers. DFT calculations indicate that the cis isomers are thermodynamically more stable by about 1–3 kcal/mol than the trans isomers. Compounds 3a , b can be converted into dithio the derivatives 5a , b and the borane complexes 6a , b , which were characterized by NMR spectroscopy and investigated by X‐ray diffraction analysis. The dialkylamino groups in 3 can be substituted by chlorine to give the chlorophosphane 7 .