Synthesis of New Hydrazones Based on 3-Hydroxy-4,8,9,11-tetramethyl-12H-6,12-methanodibenzo[d,g][1,3,2]dioxaphosphocine-2-carbaldehyde-6-oxide

A method was developed for the synthesis of first representative of unsymmetrical cage phosphonates containing a carbonyl group on the periphery. New hydrazones were prepared by the reaction of 3-hydroxy-4,8,9,11-tetramethyl-12H-6,12-methanodibenzo[d,g][1,3,2]dioxaphosphocine-2-carbaldehyde-6-oxide with hydrazines and hydrazides (phenylhydrazine, benzohydrazide, nicotinic hydrazide, isonicotinic acid hydrazide). Composition and structure of all the obtained compounds were confirmed by 1H, 13С and 31P NMR, IR spectroscopy, mass spectrometry and X-ray structural analysis. Based on 1D/2D correlation NMR experiments, it was found that the resulting hydrazones exist only as E-isomer.