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Heteropoly Acid Catalysts for the Synthesis of Fragrance Compounds from Biorenewables: Cycloaddition of Crotonaldehyde to Limonene, α‐Pinene, and β‐Pinene
Author(s) -
Costa Vinícius V.,
da Silva Rocha Kelly A.,
Mesquita Rafaela A.,
Kozhevnikova Elena F.,
Kozhevnikov Ivan V.,
Gusevskaya Elena V.
Publication year - 2013
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201300208
Subject(s) - crotonaldehyde , chemistry , pinene , cycloaddition , limonene , catalysis , organic chemistry , protonation , monoterpene , medicinal chemistry , essential oil , ion , chromatography
The interaction of widespread monoterpenes limonene, α‐pinene, and β‐pinene with crotonaldehyde using silica‐supported tungstophosphoric heteropoly acid H 3 PW 12 O 40 and its acidic cesium salt Cs 2.5 H 0.5 PW 12 O 40 as solid acid catalysts in dichloroethane solutions results in cycloaddition, which gives the same fragrant oxabicyclo[3.3.1]nonene product in a high yield. The product is likely to be formed through an α‐terpenyl carbenium ion intermediate, which is generated from monoterpene protonation and undergoes nucleophilic attack by crotonaldehyde. Both H 3 PW 12 O 40 and Cs 0.5 H 0.5 PW 12 O 40 are efficient and truly heterogeneous cycloaddition catalysts.