Synthesis and Characterization of 1‑Hydroxy-4,5-arene-Fused Tropylium Derivatives

The properties of 1-hydroxy-4,5-arene-fused tropyliums were assessed based on experimental and theoretical investigations. An X-ray crystallographic analysis revealed a decrease of bond alternation in the seven-membered ring of 1-hydroxy-4,5-benzotropylium derivatives compared with that of the paren...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2021-10, Vol.86 (19), p.13800-13807
Main Authors: Kodama, Takuya, Kawashima, Yuki, Uchida, Kenta, Deng, Zhirong, Tobisu, Mamoru
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The properties of 1-hydroxy-4,5-arene-fused tropyliums were assessed based on experimental and theoretical investigations. An X-ray crystallographic analysis revealed a decrease of bond alternation in the seven-membered ring of 1-hydroxy-4,5-benzotropylium derivatives compared with that of the parent 4,5-benzotropones, which is indicative of an increase in aromaticity upon protonation. NICS and AICD calculations also supported the increased aromaticity of 1-hydroxy-4,5-arene-fused tropylium. The pK a values for a series of 1-hydroxy-4,5-arene-fused tropylium derivatives were also determined.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01818