ISSN:
1042-7163
Keywords:
Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The structures and solid-state stereochemistry of the two P-epimeric compounds (1 and 2) formed in a reaction of butyl phenylvinylphosphinite with (-)-L-menthyl bromoacetate were studied by X-ray crystallography and CP-MAS 13C NMR spectroscopy. The two compounds were also analyzed in solution by means of 2D 1H NMR, 13C NMR, IR, UV, and dipole moment measurement techniques. Compound 1, C20H29O3P, crystallized in the orthorhombic group P 212121 with Z = 4, a = 20.491(2), b = 16.719(1), and c = 5.910(1). Compound 2, C20H29O3P, crystallized in the monoclinic space group P 21 with Z = 2, a = 9.266(1), b = 9.852(1), c = 10.954(1), and β = 95.20(1)°. In the crystals both compounds possess their C=C—P=O fragments in an s-cis array, and have their P=O and C=O dipoles oriented uniformly in a syn, nearly parallel, fashion. In solution, however, an anti arrangement of these two dipoles is slightly preferred.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hc.520020114
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