59470-47-2Relevant academic research and scientific papers
SYNTHESIS, REACTIVITY AND CONFORMATION OF 10,11-DIHYDRODIBENZO-PHOSPHEPIN AND DIBENZOPHOSPHEPIN DERIVATIVES. PHOSPHORUS ANALOGUES OF IMINOBIBENZYL ANTIDEPRESSANTS
Segall, Yoffi,Shirin, Ezra,Granoth, Itshak
, p. 243 - 254 (2007/10/02)
Derivatives of the novel dibenzophosphepin system are prepared from 10,11-dihydro-5-phenyl-5H-bibenzophosphepin 5-oxide (2).New members in the 10,11-dihydro-5H-dibenzophophepin series, including phosphorus analogues (7, 10) of the antidepressant drug imipramine (30), are also reported.Products of the nucleophilic substitution at tetrahedral phosphorus in 2 appear to be determined by the relative apicophilicity of the nucleophile.Conformational analysis based on 1H NMR data suggests folded ("butterfly") conformation for the tricyclic compounds.The twisted boat conformation of the central ring in the 10,11-dihydro compounds bears a pseudo-equatorial P=O oxygen or a P=S sulfur, in solution.Symmetric AA'BB' spin systems are found in 4, 5 and 7, and their solution conformations appear to be similar to those of analogous 10,11-dihydrodibenzoazepine derivatives.The interaction of some compounds with NMR shift reagents and their mass spectral fragmentations are discussed.
