Cyclic (1R,3R)-1,3-dimethyltrimethylene [(5R)-2-hydroxy-5-methyl-5-(2- methyl-1,3-dioxolan-2-yl)-1-cyclohexen-1-yl]-phosphonate, a stable enol.
The title compound, C16H27O6P, was obtained from the rearrangement of the corresponding vinyl phosphate. 31P NMR experiments in solution have shown that this compound equilibrates to a mixture of three isomers in nearly equal proportions. In the crystalline state a single isomer is found which diffraction analysis identified as the enol form of the beta-keto phosphonate having R stereochemistry at atom C(8).
Capron
M A
MA
Department of Chemistry, University of Iowa, Iowa City 52242, USA.
An
J
J
Swenson
D C
DC
Wiemer
D F
DF
D003460:Crystallization; D003510:Cyclohexanes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D003510:Cyclohexanes; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D014753:Vinyl Compounds; C093471:cyclic-1,3-dimethyltrimethylene (2-hydroxy-5-methyl-5-(2-methyl-1,3-dioxolan-2-yl)-1-cyclohexen-1-yl)phosphonate; C049436:vinyl phosphate