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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

Authors :
Leyong Wang
Guoli Huang
Juli Jiang
Shao-Lu Li
Ming-Yu Teng
Ying Liu
Source :
RSC Advances. 3:9016
Publication Year :
2013
Publisher :
Royal Society of Chemistry (RSC), 2013.

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, ΔS‡373 K = 37.7 J mol−1 K−1, and ΔG‡373 K = 85.6 kJ mol−1 by Eyring plot analysis.

Details

ISSN :
20462069
Volume :
3
Database :
OpenAIRE
Journal :
RSC Advances
Accession number :
edsair.doi...........5021e42c01dca5be89eb1261d2bf9362
Full Text :
https://doi.org/10.1039/c3ra41273c