Single crystal X-ray diffraction of dimethyl α-chloromethyl-α-hydroxybenzylphosphonate shows the compound to exist as hydrogen-bonded dimers in the solid state. In solution, 1H and 13C nmr spectroscopy reveal chemical shift non-equivalence of the corresponding nuclei in the two alkoxy groups of dialkyl α-hydroxybenzyl- and dialkyl α-methoxybenzylphosphonates, an effect that is attributed primarily to the presence of the chiral α-carbon atom, although restriction of rotation about the P-Cα bond by intermolecular hydrogen-bonding may also be a factor in the α-hydroxy compounds. Chemical shift non-equivalence of the α-halogenomethyl protons in dimethyl α-halogenomethyl-α-hydroxyben-zylphosphonates is significantly greater for the chloro- than for the bromo-compound.
|Number of pages||5|
|Journal||Phosphorus, Sulfur, and Silicon and the Related Elements|
|Publication status||Published - jún. 1 1993|
ASJC Scopus subject areas
- Organic Chemistry
- Inorganic Chemistry