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Synthesis and structural assignment of 2,4′-disubstituted benzylidenefluorenes and 4′-substituted benzylidene-1-azafluorenes

✍ Scribed by Rita Annunziata; Valentina Molteni; Laura Raimondi

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
261 KB
Volume
36
Category
Article
ISSN
0749-1581

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✦ Synopsis

In the course of a study aimed at the investigation of edge-to-face areneÈarene interactions, substituted benzylideneÑuorenes 8È16 and benzylidene-1-azaÑuorenes 20È24 were synthesized as mixtures of EÈZisomers. The full structural assignment of these compounds, performed by 2D NMR experiments, is described together with a study of their EÈZ isomerization under equilibrating conditions. For compounds 8È16 no correlation was observed between the electron-donating or electron-withdrawing nature of the substituent groups and the E/Z equilibrium ratios. In the case of 20È24 the predominance of the E-isomers seems to depend exclusively on the N-lone pairÈbenzylidene ring electronic repulsion rather than on the nature of the para substituent on the aromatic ring.

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✍ Guoxiong Hua; Yang Li; Amy L. Fuller; Alexandra M. Z. Slawin; J. Derek Woollins 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 325 KB

## Abstract The reaction of hydrazide with carbonyl chloride in the presence of sodium carbonates leads to the corresponding 1,2‐diacylhydrazines [**1a**–**t**, R^1^C(O)NHNHC(O)R^2^, R^1^ = aryl, R^2^ = aryl or alkyl] in moderate to excellent yield (57–90 %). The latter reacts with 2,4‐diphenyl‐1,3