Synthesis of bis(trifluoromethyl)-substituted olefins: Methods of preparation and properties

Synthesis of bis(trifluoromethyl)-substituted olefins: Methods of preparation and properties

Several bis(trifluoromethyl)‐ and trifluoromethyl‐substituted alkenes, dienes, arylalkenes, and α,β‐unsaturated derivatives of carbonyl compounds such as tosylhydrazone 5b and diazomethane 5c were prepared. Their reactivity towards a variety of nucleophiles, resulting from the electron‐withdrawing e...

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Veröffentlicht in:Liebigs Annalen 1995-11, Vol.1995 (11), p.2027-2035
Hauptverfasser: Haas, Alois, Lieb, Max, Zwingenberger, Jörg
Format: Artikel
Sprache:eng
Schlagworte:
Acceptor-substituted double bond
anti-Michael addition
Charge-shift correlation
Steric demand of a CF3 group
Trifluoromethyl-substituted alkenes
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container_title Liebigs Annalen
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creator Haas, Alois
Lieb, Max
Zwingenberger, Jörg
description Several bis(trifluoromethyl)‐ and trifluoromethyl‐substituted alkenes, dienes, arylalkenes, and α,β‐unsaturated derivatives of carbonyl compounds such as tosylhydrazone 5b and diazomethane 5c were prepared. Their reactivity towards a variety of nucleophiles, resulting from the electron‐withdrawing effect of the trifluoromethyl group, was investigated. Depending on the trifluoromethyl‐ and a bis(trifluoromethyl)‐substituted double bond, different regioselectivities were observed in the reaction with morpholinocyclohexene as a nucleophile. An explanation is given on the basis of the 13C‐NMR data.
doi_str_mv 10.1002/jlac.1995199511284
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source Wiley Online Library Journals Frontfile Complete
subjects Acceptor-substituted double bond
anti-Michael addition
Charge-shift correlation
Steric demand of a CF3 group
Trifluoromethyl-substituted alkenes
title Synthesis of bis(trifluoromethyl)-substituted olefins: Methods of preparation and properties
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