Facile synthesis of 3-(trifluoromethyl)adamantane derivatives

[Display omitted] •An effective synthesis for 1-fluoro-3-(trifluoromethyl)adamantane is proposed.•1-Fluoro-3-(trifluoromethyl)adamantane can be prepared in a multi-gram amount starting from commercially available 3-hydroxyadamantane-1-carboxylic acid.•1-Fluoro-3-(trifluoromethyl)adamantane can be us...

Full description

Saved in:
Bibliographic Details
Published in:Journal of fluorine chemistry 2017-09, Vol.201, p.11-14
Main Authors: Zhyhadlo, Yevheniia Y., Gaidai, Alexander V., Levandovskiy, Igor A., Bezdudny, Andriy V., Rassukana, Yuliya V.
Format: Article
Language:English
Subjects:
Adamantane
Amines
Carboxylic acids
Derivatives
Fluorination
Fluorine
Functional groups
Hydrocarbons
Sulfur
Sulfur tetrafluoride
Synthesis
Trifluoromethyl
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:[Display omitted] •An effective synthesis for 1-fluoro-3-(trifluoromethyl)adamantane is proposed.•1-Fluoro-3-(trifluoromethyl)adamantane can be prepared in a multi-gram amount starting from commercially available 3-hydroxyadamantane-1-carboxylic acid.•1-Fluoro-3-(trifluoromethyl)adamantane can be used for preparation of (trifluoromethyl)adamantane derivatives (acids, amines, etc.).•The transformations involving participation of fluorine atom at bridgehead position of adamantane were revealed. A facile synthesis for 1-fluoro-3-(trifluoromethyl)adamantane, based on fluorination of 3-hydroxyadamantane-1-carboxylic acid, was developed. Its synthetic potentialities for preparation of (trifluoromethyl)adamantane derivatives containing diverse functional groups (acids, amines, etc.) in a bridgehead position, were disclosed.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2017.07.009