Development of Nitrolactonization Mediated by Iron(III) Nitrate Nonahydrate

Tomoyuki Yoshimura; Yuki Umeda; Risako Takahashi; Jun-ichi Matsuo

doi:10.1248/cpb.c20-00645

Regular Articles

Development of Nitrolactonization Mediated by Iron(III) Nitrate Nonahydrate

Tomoyuki Yoshimura , Yuki Umeda, Risako Takahashi, Jun-ichi Matsuo

Author information

Keywords: nitrolactonization, iron(III) nitrate nonahydrate, nitrogen dioxide, radical intermediate

JOURNAL FREE ACCESS FULL-TEXT HTML
Supplementary material

2020 Volume 68 Issue 12 Pages 1220-1225

DOI https://doi.org/10.1248/cpb.c20-00645

Details

Abstract

The nitrolactonization of alkenyl carboxylic acids mediated by Fe(NO₃)₃·9H₂O has been developed. Nitrolactones were obtained in up to 93% yield by treatment of alkenyl carboxylic acids with Fe(NO₃)₃·9H₂O. Mechanistic studies disclosed that the reaction proceeded through a radical intermediate generated from addition of NO₂ to alkenyl carboxylic acids.

Graphical Abstract Fullsize Image

Corresponding author

Register with J-STAGE for free!