NMR Studies on [2 + 3] Cycloaddition of Nitrile Oxides to Polyunsaturated Medium Size Rings

Mirosław Gucma, Wiesław Marek Gołębiewski, Alicja K. Michalczyk
2016 Journal of the Brazilian Chemical Society  
Site selectivity, regioselectivity and stereoselectivity of [2 + 3] cycloaddition of 4-trifluoromethylbenzonitrile oxide to polyunsaturated medium size rings including 1,5,9-cyclododecatriene, 11-membered sesquiterpenes, 1,3-cyclooctadiene and 5-vinyl-2norbornene were examined. Site selectivity was correlated with electron charges of alkenyl carbon atoms. Structure of the products has been established by an extensive application of 1D and 2D 1 H and 13 C nuclear magnetic resonance (NMR)
more » ... copy and electrospray ionization mass spectrometry. Some of the obtained products showed moderate fungicidal activities.
doi:10.5935/0103-5053.20160078 fatcat:qyzgw45aprbbdkwnb6watt6ode