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Synthesis and spectroscopic studies of 2‐(1,1‐dimethylhydrazono)propyl phosphonates
Author(s) -
Salazar Miguel,
Li VenShun,
Cates Lindley A.
Publication year - 1988
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260260607
Subject(s) - chemistry , phosphonate , derivative (finance) , stereochemistry , nuclear magnetic resonance spectroscopy , spectroscopy , medicinal chemistry , organic chemistry , financial economics , economics , physics , quantum mechanics
Abstract The synthesis of diethyl 2‐(1,1‐dimethylhydrazono)propyl phosphonate (1) and its 1‐benzoyl derivative (2) is described. The 1 H and 13 C NMR spectra of 1 and 2 have been completely assigned with the aid of two‐dimensional 1 H 13 C correlation NMR spectroscopy. Spectral data for ethyl α‐benzoyl‐β‐(1,1‐dimethylhydrazino)crotonate (5) were also obtained. The results show that 1 exists predominantly in the E ‐ and Z ‐isomeric forms in a ratio of ca 2:1, and 2 occurs almost exclusively in the E ‐form. Data for 5 indicate that this compound exists in the Z ‐ and E ‐forms in a ratio of ca 3:1.