Synthesis
DOI: 10.1055/a-1681-4823
feature

1,3-Bis(trifluoromethyl)prop-2-ene 1-Iminium Salts: Reactions with Alkoxybenzenes and Anilines

Michael Keim
,
Medina Jasarevic
,
Ines Miller
,
This work was supported by Ulm University.


In memoriam Prof. Dr. Manfred Regitz

Abstract

1,3-Bis(trifluoromethyl)prop-2-ene 1-iminium triflate salts were prepared for the first time and some synthetic applications as 1,3-biselectrophilic building blocks were established. They were found to react with dimethoxybenzenes or methylene-1,2-dioxybenzenes to furnish vinylogous trifluoroacetylation products (4-aryl-1,1,1,5,5,5-hexafluoropent-3-en-2-ones) and 1-dialkylamino-1,3-bis(trifluoromethyl)-1H-indenes. With aniline and ring-substituted anilines, 2,4-bis(trifluoromethyl)quinolines were formed. An unusual 4H-pyran, formally a condensation product of the N,N-dimethyl-1,3-bis(trifluoromethyl)prop-2-en-1-iminium ion and its enaminone precursor, is also reported.

Supporting Information



Publication History

Received: 28 September 2021

Accepted after revision: 28 October 2021

Publication Date:
28 October 2021 (online)

© 2021. Thieme. All rights reserved

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