Stereoselective nitration of asymmetric hydrazones with nitric oxide

Nitration of asymmetric hydrazones with nitric oxide occurred stereoselectively at C1′-atom, giving mono-nitrated trans isomer as a major outcome. The ratio of trans to cis was up to >99. Higher isolated yields of nitrated products and higher trans/cis ratios of isomers suggest that this procedure offers advantages for synthesizing asymmetry nitro compounds.

Nitration of asymmetric hydrazones with nitric oxide occurred stereoselectively, giving mono-nitrated trans isomer as a major outcome. The ratio of trans to cis was up to >99.Figure optionsDownload as PowerPoint slide