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

Abstract

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.