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Issue 23, 2013
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Synthesis, chemo-selective properties of substituted 9-aryl-9H-fluorenes from triarylcarbinols and enantiomerical kinetics of chiral 9-methoxy-11-(naphthalen-1-yl)-11H-benzo[a]fluorene

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Abstract

9-Aryl-fluorenes were synthesized conveniently from triarylcarbinols in the presence of TsOH. Notably, the orientation of the intramolecular aromatic substitution reaction was dictated by the nature of the substituents on the aryl rings of triarylcarbinols, owing to electronic and conjugated effects. In particular, triarylcarbinols with (3-methoxy)phenyl and naphthalenyl groups formed benzo[a]fluorenes selectively. Moreover, 9-methoxy-11-(naphthalen-1-yl)-11H-benzo[a] fluorene (2g), with a center of chirality, exists as a mixture of diastereoisomers, due to the restricted rotation of a C–C single bond. First-order rate constants for the enantiomerization of 2g in DMSO were obtained over the temperature from 297 K to 393 K, and thermodynamic parameters were determined as ΔH = 99.7 kJ mol−1, ΔS373 K = 37.7 J mol−1 K−1, and ΔG373 K = 85.6 kJ mol−1 by Eyring plot analysis.

Graphical abstract: Synthesis, chemo-selective properties of substituted 9-aryl-9H-fluorenes from triarylcarbinols and enantiomerical kinetics of chiral 9-methoxy-11-(naphthalen-1-yl)-11H-benzo[a]fluorene

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Supplementary files

Article information


Submitted
17 Mar 2013
Accepted
03 Apr 2013
First published
08 Apr 2013

RSC Adv., 2013,3, 9016-9022
Article type
Paper

Synthesis, chemo-selective properties of substituted 9-aryl-9H-fluorenes from triarylcarbinols and enantiomerical kinetics of chiral 9-methoxy-11-(naphthalen-1-yl)-11H-benzo[a]fluorene

M. Teng, Y. Liu, S. Li, G. Huang, J. Jiang and L. Wang, RSC Adv., 2013, 3, 9016 DOI: 10.1039/C3RA41273C

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