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Synthesis of bis(trifluoromethyl)‐substituted olefins: Methods of preparation and properties
Author(s) -
Haas Alois,
Lieb Max,
Zwingenberger Jörg
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199511284
Subject(s) - trifluoromethyl , chemistry , diazomethane , nucleophile , reactivity (psychology) , double bond , organic chemistry , medicinal chemistry , catalysis , alkyl , medicine , alternative medicine , pathology
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 13 C‐NMR data.