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A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives
Author(s) -
Moni Lisa,
Banfi Luca,
Basso Andrea,
Mori Alessia,
Risso Federica,
Riva Renata,
Lambruschini Chiara
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100064
Subject(s) - photoisomerization , chemistry , photostationary state , amide , ferulic acid , organic chemistry , primary (astronomy) , isomerization , catalysis , food science , astronomy , physics
A thorough study on the ( E ) to ( Z ) photoisomerization of ferulic acid derivatives (esters, amides of all types, and ketones) was carried out. At the photostationary state, only aliphatic or benzylic tertiary amides reach a nearly complete conversion of ( E ) isomers into the ( Z ) ones, whereas for esters, primary and secondary amides or aromatic tertiary amides mixtures of ( Z )/( E ) ranging from 7 : 93 to 72 : 28 are observed. Ketones show rather limited photoisomerization. However, ( Z ) ketones may be obtained by the reaction of organometal compounds with an isomerized ( Z ) Weinreb amide.