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1-Aryl-F-1,3-butadienes and Unsymmetrical α,ω-Diaryl-F-polyenes
journal contribution
posted on 1997-05-16, 00:00 authored by Alexander B. Shtarev, Mikhail M. Kremlev, Zdenek ChvátalPara-substituted
1-aryl-F-1,3-butadiene derivatives
p-R-C6H4-CFCFCFCF2
(2a−g), where R =
H, CH3, OCH3, OC6H11,
N(CH3)2, Br, and CF3, have been
prepared by reaction of appropriate
arylmagnesium bromides with F-1,3-butadiene.
19F NMR chemical shifts correlate with
σp Hammett
substituent constants. Compounds
2a−e react on their terminal
perfluorovinyl group with
C-nucleophiles and were used as intermediates in subsequent reactions
with suitable organolithium
compounds for the synthesis of a new series of unsymmetrically
substituted α,ω-diaryl-F-polyenes
RC6H4(CFCF)nC6H4R‘,
where n = 2 or 3 and R‘ is one of the substituents
specified above. A
variety of new synthons containing
α,ω-diaryl-F-1,3-butadiene skeleton and reactive Br, OH,
CHO,
and COOH functionalities in para-positions on aromatic rings
has been also prepared. Structural
aspects, NMR spectra, and mesogenic properties of the title compounds
are discussed.
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Keywords
polyenes RC 6 H 419 F NMR chemical shiftsσ p Hammett substituent constantstitle compoundsOC 6 H 11reactive BrCompounds 2COOH functionalitiesNMR spectraterminal perfluorovinyl groupStructural aspectsmesogenic propertiesCH 3organolithium compoundspolyenes ParadiarylbutadieneOCH 3CF 3arylmagnesium bromides
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