20988-88-9Relevant academic research and scientific papers
A trans-Folded Alkene System: Synthesis, Structure and Isomerization of 2,2'-Diaryl-1,1'-bi(1,2-dihydrophthalazinylidenes)
Butler, Richard N.,Gillan, Ann M.,Lysaght, Fiona A.,McArdle, Patrick,Cunningham, D.
, p. 555 - 564 (2007/10/02)
A series of 2,2'-diaryl-1,1'-bi(1,2-dihydrophthalazinylidenes) have been synthesized from 1-hydroxy-2-aryl-1,2-dihydrophthalazines.An X-ray crystal structure showed relief of strain in these new ylidenes by a trans-folding of the alkene linkage.The mechanism of their formation was probed with additives such as sulphur, N-phenylmaleimide, and dimethyl acetylenedicarboxylate which interacted with intermediates in the reaction and gave further interesting new ylidene structures.The mechanism of trans-cis isomerization of the biphthalazinylidenes was studied using 270 MHz 1 H-NMR spectroscopy to measure the kinetics and activation parameters for the isomerization.X-Ray crystal structures of the following compounds are reported: 2,2'(p-bromophenyl)-trans-1,1'-bi--4--1-phenyl-3,4-dihydropyrrole-2,5-dione, (10d); dimethyl 3-(2-phenyl-1,2-dihydrophthalazin-1-ylidene)-2-oxobutanedioate (11), and dimethyl 2-acetoxy-3-(2-phenyl-1,2-dihydrophthalazin-1-yl)but-2-ene-1,4-dioate (12).
