Synthesis, spectral studies, antimicrobial and insect antifeedant potent keto oxiranes

Abstract

A series of ee (αS, βR) biphenyl keto oxiranes (biphenyl-4-yl[3-(substituted phenyl)oxiran-2-yl]methanones) have been synthesized by phase transfer catalysed epoxidation of biphenyl 2E-chalcones. The yields of oxiranes are more than 95%. The synthesized oxiranes have been characterized by IR, 1H, 13C and GC–MS spectra. The spectral data are correlated with Hammett substituent constants and Swain–Lupton parameters. From the regression analyses, the effect of substituent on the group frequencies has been predicted. The antimicrobial and insect antifeedant activities of all synthesized oxiranes have been evaluated.

Keywords

• Biphenyl keto oxiranes
• Synthesis
• IR and NMR spectra
• Substituent effects
• Antimicrobial and insect antifeedant activities