CF(3)‐Containing para‐Quinone Methides for Organic Synthesis

A new family of CF(3)‐containing para‐quinone methides (CF(3)‐QMs) was systematically investigated for its suitability in organic synthesis. Addition of different nucleophiles gives access to target molecules with a benzylic CF(3)‐containing stereogenic center straightforwardly. The electrophilicity...

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Autores principales: Winter, Michael, Schütz, Roman, Eitzinger, Andreas, Ofial, Armin R., Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7335660/
https://www.ncbi.nlm.nih.gov/pubmed/32624681
http://dx.doi.org/10.1002/ejoc.202000295
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author Winter, Michael
Schütz, Roman
Eitzinger, Andreas
Ofial, Armin R.
Waser, Mario
author_facet Winter, Michael
Schütz, Roman
Eitzinger, Andreas
Ofial, Armin R.
Waser, Mario
author_sort Winter, Michael
collection PubMed
description A new family of CF(3)‐containing para‐quinone methides (CF(3)‐QMs) was systematically investigated for its suitability in organic synthesis. Addition of different nucleophiles gives access to target molecules with a benzylic CF(3)‐containing stereogenic center straightforwardly. The electrophilicity parameter E of the prototypical CF(3)‐QM 2,6‐di‐tert‐butyl‐4‐(2,2,2‐trifluoroethylidene)cyclohexa‐2,5‐dien‐1‐one was determined to be –11.68 according to the Mayr scale, making it one of the most reactive quinone methides known so far.
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spelling pubmed-73356602020-07-07 CF(3)‐Containing para‐Quinone Methides for Organic Synthesis Winter, Michael Schütz, Roman Eitzinger, Andreas Ofial, Armin R. Waser, Mario European J Org Chem Full Papers A new family of CF(3)‐containing para‐quinone methides (CF(3)‐QMs) was systematically investigated for its suitability in organic synthesis. Addition of different nucleophiles gives access to target molecules with a benzylic CF(3)‐containing stereogenic center straightforwardly. The electrophilicity parameter E of the prototypical CF(3)‐QM 2,6‐di‐tert‐butyl‐4‐(2,2,2‐trifluoroethylidene)cyclohexa‐2,5‐dien‐1‐one was determined to be –11.68 according to the Mayr scale, making it one of the most reactive quinone methides known so far. John Wiley and Sons Inc. 2020-03-30 2020-07-07 /pmc/articles/PMC7335660/ /pubmed/32624681 http://dx.doi.org/10.1002/ejoc.202000295 Text en © 2020 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Winter, Michael
Schütz, Roman
Eitzinger, Andreas
Ofial, Armin R.
Waser, Mario
CF(3)‐Containing para‐Quinone Methides for Organic Synthesis
title CF(3)‐Containing para‐Quinone Methides for Organic Synthesis
title_full CF(3)‐Containing para‐Quinone Methides for Organic Synthesis
title_fullStr CF(3)‐Containing para‐Quinone Methides for Organic Synthesis
title_full_unstemmed CF(3)‐Containing para‐Quinone Methides for Organic Synthesis
title_short CF(3)‐Containing para‐Quinone Methides for Organic Synthesis
title_sort cf(3)‐containing para‐quinone methides for organic synthesis
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7335660/
https://www.ncbi.nlm.nih.gov/pubmed/32624681
http://dx.doi.org/10.1002/ejoc.202000295
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AT ofialarminr cf3containingparaquinonemethidesfororganicsynthesis
AT wasermario cf3containingparaquinonemethidesfororganicsynthesis

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