A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives. Issue 11 (15th March 2021)

• Record Type: Journal Article
• Authors: Moni, Lisa; Banfi, Luca; Basso, Andrea; Mori, Alessia; Risso, Federica; Riva, Renata; Lambruschini, Chiara
• Is Part Of: European journal of organic chemistry. Issue 11(2021)
• Page Start: 1737
• Page End: 1749
• Publication Date: 2021-03-15
• Subjects: Amides -- Biomass -- Isomerization -- Natural products -- Photochemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100064
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : A comprehensive study of photoisomerzation of ferulic acid derived esters, amides, and ketones was carried out. Only in the case of aliphatic tertiary amides, a nearly complete E→Z conversion was achieved.