Issue 7, 2003

A novel approach of cycloaddition of difluorocarbene to α,β-unsaturated aldehydes and ketones: synthesis of gem-difluorocyclopropyl ketones and 2-fluorofurans

Abstract

A series of gem-difluorocyclopropyl acetals and ketals are easily obtained in moderate yields from the [1+2] cycloaddition of difluorocarbene to 1,3-dioxolanes of α,β-unsaturated aromatic aldehydes and ketones. Hydrolysis of these fluorinated compounds under acidic conditions either gives the corresponding gem-difluorocyclopropyl ketones or 1-aryl-2-fluorofuran derivatives through intramolecular carbonium rearrangement with simultaneous ring cleavage.

Graphical abstract: A novel approach of cycloaddition of difluorocarbene to α,β-unsaturated aldehydes and ketones: synthesis of gem-difluorocyclopropyl ketones and 2-fluorofurans

Supplementary files

Article information

Article type
Paper
Submitted
12 Dec 2002
Accepted
19 Feb 2003
First published
11 Mar 2003

Org. Biomol. Chem., 2003,1, 1151-1156

A novel approach of cycloaddition of difluorocarbene to α,β-unsaturated aldehydes and ketones: synthesis of gem-difluorocyclopropyl ketones and 2-fluorofurans

W. Xu and Q. Chen, Org. Biomol. Chem., 2003, 1, 1151 DOI: 10.1039/B212232D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements