Rotational Isomerism in Fluorene Derivatives XII. : Conformational Equilibria of 9-Substituted 9-(2-methoxymethylphenyl) fluorenes
Memoirs of the Faculty of Engineering, Yamaguchi University Volume 38 Issue 2
Page 269-276
published_at 1988
Title
フルオレン誘導体の回転異性 : 第 12 報 9-置換 9-(2-メトキシメチルフェニル)フルオレン誘導体の配座平衡
Rotational Isomerism in Fluorene Derivatives XII. : Conformational Equilibria of 9-Substituted 9-(2-methoxymethylphenyl) fluorenes
Creators
Nishida Akiko
Creators
Shirakawa Shinsuke
Creators
Fujisaki Shizuo
Creators
Kajigaeshi Shoji
Source Identifiers
A series of 9-(2-methoxymethylphenyl) fluorenes [4] (9-hydro-[4a], 9-hydroxyl-[4b]. 9-methyl-[4c], 9-acetyl-[4d], 9-benzoyl-[4e], 9-carboxyl-[4f], 9-methoxycarbonyl-[4g] and 9-methoxyl-9-(2-methoxymethylphenyl) fluorene [4h] were prepared, and their conformational equilibria between ap and sp were investigated and compaired with that of known 9-substituted 9-(2-methoxyphenyl) fluorenes [1]. It was confirmed that [4a] existed as predominant sp conformer (ap/sp=1/4.1) at room temperature, and [4b] as approximately equal proportions of two conformers (ap/sp=1.5/1) at -58℃ on their NMR spectra, respectively. In the case of [4b], we inferred that the formation of intramolecular hydrogen bond would be difficult, because the degree of freedom of 2'-substituent was increased than that of [1b]. Further, the existence of attractive interaction between methoxyl-oxygen and carbonyl-carbon in [4e] was recognized on its NMR spectrum at low temperature.
Languages
jpn
Resource Type
departmental bulletin paper
Publishers
山口大学工学部
Date Issued
1988
File Version
Version of Record
Access Rights
open access
Relations
[ISSN]0372-7661
[NCID]AN00244228
Schools
工学部