A New Synthetic Approach to α-Chlorocinnamaldehydes

Valentine G. Nenajdenko; Alexander L. Reznichenko; Olesya N. Lenkova; Alexey V. Shastin; Elizabeth S. Balenkova

doi:10.1055/s-2004-837303

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Synthesis 2005(4): 605-609
DOI: 10.1055/s-2004-837303

PAPER

A New Synthetic Approach to α-Chlorocinnamaldehydes

Valentine G. Nenajdenko*^a, Alexander L. Reznichenko^a, Olesya N. Lenkova^a, Alexey V. Shastin^b, Elizabeth S. Balenkova^a
^a Moscow State University, Department of Chemistry, Leninskie Gory, Moscow 119992, Russia
^b Institute of Problems of Chemical Physics, Chernogolovka, Moscow region, 142432, Russia
Fax: +7(095)9328846; e-Mail: nen@acylium.chem.msu.ru ;

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Publication History

Received 20 October 2004
Publication Date:
22 December 2004 (online)

Abstract
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Abstract

A new simple and efficient transformation of aromatic aldehydes into α-chlorocinnamaldehydes is described. Catalytic olefination reaction of hydrazones of aromatic aldehydes with 2-trichloromethyl-1,3-dioxolane gives ethylene acetals of target alkenes in moderate to good yields. The reaction proceeds stereoselectively to form preferably Z-isomers.

Key words

catalytic olefination - α-chlorocinnamaldehydes - catalysis - alkenes - 2-trichloromethyl-1,3-dioxolane

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