Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones
Issued Date
2022-09-01
Resource Type
ISSN
09365214
eISSN
14372096
Scopus ID
2-s2.0-85128893329
Journal Title
Synlett
Volume
33
Issue
14
Start Page
1323
End Page
1328
Rights Holder(s)
SCOPUS
Bibliographic Citation
Synlett Vol.33 No.14 (2022) , 1323-1328
Suggested Citation
Phae-Nok S., Kuhakarn C., Leowanawat P., Reutrakul V., Soorukram D. Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones. Synlett Vol.33 No.14 (2022) , 1323-1328. 1328. doi:10.1055/a-1792-7169 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/84169
Title
Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones
Author's Affiliation
Other Contributor(s)
Abstract
Decarboxylative transformations of paraconic acids, a class of γ-butyrolactones containing a carboxylic acid group at the β-position as their characteristic functionality, by using a combination of Ag- NO3/K2S2O8 were investigated. The dual function of AgNO3 as an initiator of the decarboxylation process and as a source of nitrogen dioxide radicals that react with aliphatic carboxylic substrates is reported for the first time. Starting from paraconic acids, β-nitro- and β-hydroxy γ-butyrolactones were obtained in good combined yields (41 85%) with moderate selectivity in a one-pot operation. The reactions were completed within an acceptable reaction time (two hours) under mild conditions that were tolerated by the γ-butyrolactone core. This study provides a direct and site-specific entry to β-nitro- and β-hydroxy γ-butyrolactones, which are important precursors in organic transformations.