Heteropoly Acid Catalysts for the Synthesis of Fragrance Compounds from Biorenewables: Cycloaddition of Crotonaldehyde to Limonene, α‐Pinene, and β‐Pinene | Zendy

Costa Vinícius V. | Zendy; da Silva Rocha Kelly A. | Zendy; Mesquita Rafaela A. | Zendy; Kozhevnikova Elena F. | Zendy; Kozhevnikov Ivan V. | Zendy; Gusevskaya Elena V. | Zendy

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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.

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