Synthesis, spectral studies, antimicrobial, antioxidant and insect antifeedant activities of some 9H-fluorene-2-yl keto-oxiranes

Thirteen ee (αS, βR) 9H-fluorene-2-yl keto-oxiranes (2-(9H)-fluorene-4-yl[3-(substituted phenyl)oxiran-2-yl]methanones) have been synthesized by phase transfer catalysed epoxidation of 9H-fluorene-2-yl chalcones. The yields of oxiranes are more than 95%. The synthesized oxiranes have been characterized by IR, (1)H, (13)C and GC-MS spectral data. The spectral data are correlated with Hammett substituent constants and Swain-Lupton parameters. From the regression analysis, the effect of substituents on the group frequencies has been predicted. The antimicrobial, antioxidant and insect antifeedant activities of all the synthesized oxiranes have been studied.