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language
eng
Author
Sakai, Takuya
Kumoi, Takuma
Ishikawa, Tatsuro
Nitta, Takahiro
Description
A series of flavinium salts, 5-ethylisoalloxazinium, 5-ethylalloxazinium, and 1,10-ethylene-bridged alloxazinium triflates, were prepared from commercially available riboflavin. This study presents a comparison between their optical and redox properties, and their catalytic activity in H2O2 oxidations of sulfide, tertiary amine, and cyclobutanone. Reflecting the difference between the π-conjugated ring structures, the flavinium salts displayed very different redox properties, with reduction potentials in the order of: 5-ethylisoalloxazinium > 5-ethylalloxazinium > 1,10-ethylene-bridged alloxazinium. A comparison of their catalytic activity revealed that 5-ethylisoalloxazinium triflate specifically oxidises sulfide and cyclobutanone, and 5-ethylalloxazinium triflate smoothly oxidises tertiary amine. 1,10-Bridged alloxazinium triflate, which can be readily obtained from riboflavin in large quantities, showed moderate catalytic activity for the H2O2 oxidation of sulfide and cyclobutanone.
Journal Title
Organic & Biomolecular Chemistry
Volume
16
Issue
1621
Start Page
3999
End Page
4007
ISSN
1477-0520
ISSN(Online)
1477-0539
Published Date
2018-5-30
DOI
PubMed ID
Publisher
Royal Society of Chemistry
NII Type
Journal Article
Format
PDF
Text Version
著者版
Gyoseki ID
e33534
OAI-PMH Set
Faculty of Science and Engineering