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Synthesis of cis-Cinnamic Acid from trans-Cinnamaldehyde over Ag+-Exchanged Beta-Zeolite in Toluene

Authors: Takashi YAMASHIRO; Ryoji YOSHIDA; Takashi TAKAHASHI; Kanji SATO; Masayuki NOMURA; Masataka OGASAWARA; Sumio KATO; +1 Authors

Synthesis of cis-Cinnamic Acid from trans-Cinnamaldehyde over Ag+-Exchanged Beta-Zeolite in Toluene

Abstract

With a view to promoting green chemistry, cis-cinnamic acid (cis-CA) has been synthesized by using Ag-exchanged zeolites (AGZ). cis-CA [(Z)-3-phenyl-2-propenoic acid] and derivatives are physiologically active substances having plant growth regulatory activity, and have recently been isolated from plants[1,2]. Methods of synthesizing cis-CA reported up to now include photoisomerization of trans-cinnamic acid [the (E)-form, trans-CA], the method of reacting (Z)-2-bromostyrene with carbon monoxide in the presence of a palladium triphenylphosphine phasetransfer catalyst[3], and the method of electrolytic carboxylation of 2-bromostyrene using a nickel catalyst[4]. On the other hand, silver ion (Ag) -exchanged zeolite, silver ion supported on porous material[5] and complex membranes made up of amino acids and silver polymers[6] and the like have been utilized as olefin separation agents. In the present study, cis-CA was prepared in one pot synthesis using AGZ in toluene by novel methods of isomerization and oxidation of trans-cinnamaldehyde (TCA) to cis-CA exploiting the fact that Ag soft Lewis acid on AGZ forms a π -complex with the olefin double bond of TCA and reacts as the oxidant. (Scheme 1)

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citations
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
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