Synthesis of α-Nitro Ketoximes from Styrenes and tert-Butyl Nitrite

Abstract

We have discovered that various α-nitro ketoximes can be synthesized in good yields starting from styrenes and tert-butyl nitrite. The success of the reaction was critically dependent on the use of a mixture solvent of dimethylsulfoxide and water. The reaction can tolerate a wide variety of substituents including electron-withdrawing and electron-donating groups.

GRAPHICAL ABSTRACT

Keywords:

• Free radical
• α-nitro ketoxime
• NO
• styrene
• tert-butyl nitrite

SUPPLEMENTAL MATERIAL

Full experimental details, ¹H NMR and ¹³C NMR spectra, and references for all the products can be accessed on the publisher’s website.