An Efficient Modular Synthesis of Conjugated ω-(p-Hexyloxyphenyl)-polyenals

Beata W. Domagalska; Ludwik Syper; Kazimiera A. Wilk

doi:10.1055/s-2001-18711

PAPER

An Efficient Modular Synthesis of Conjugated ω-(p-Hexyloxyphenyl)-polyenals

Beata W. Domagalska^a, Ludwik Syper^b, Kazimiera A. Wilk*^a
^a Institute of Organic and Polymer Technology, Wrocław University of Technology, Wybrzeře WyspiaŇskiego 27, 50-370 Wrocław, Poland
Fax: +48(71)3203678; e-Mail: kaw@itots.ch.pwr.wroc.pl;
^b Institute of Organic Chemistry, Biochemistry and Biotechnology, Wrocław University of Technology, Wybrzeře WyspiaŇskiego 27, 50-370 Wrocław, Poland

Abstract

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Abstract

Convenient precursors (α,β-unsaturated aldehydes 1-5) for all-E conjugated ω-(p-hexyloxyphenyl)polyenals having two (15), four (16), five, (19), six (17) and eight (18) conjugated double bonds were synthesized in a modular synthesis using reactive silyl enol ethers [1-(trimethylsilyloxy)-1,3-butadiene or 1-(trimethylsilyloxy)-1,3,5-hexatriene)] as building blocks, and 5,5-diethoxypenta-2-enal (1) as a template. Polyene 8 containing three conjugated double bonds in its structure was obtained from ω-(p-hexyloxyphenyl)propenal (6) and butadienyl ethyl ether as starting materials.

Key words

acetals - aldehydes - aldol reactions - alkenes - eliminations

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Referenzen

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