Optically active phosphine oxides: 10 [1]; X-ray structure and conformation of (Sp)- and (Rp)-L-menthyl α-(phenylvinylphosphinyl)acetates
✍ Scribed by K. Michał Pietrusiewicz; Maria Zabłocka; Maciej KuoáZnikowski; Wanda Wieczorek; Waldemar Maniukiewicz; Maria Rospenk
- Book ID
- 102846416
- Publisher
- John Wiley and Sons
- Year
- 1991
- Tongue
- English
- Weight
- 776 KB
- Volume
- 2
- Category
- Article
- ISSN
- 1042-7163
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✦ Synopsis
The structures and solid-state stereochemistry of the two P-epimeric compounds (1 and 2 ) formed in a reaction o f butyl phenylvinylphosphinite with ( -)-L- menthvl bromoacetate were studied by X-ray crystallography and CP-MAS I3C N M R spectroscopy. The two compounds were also analyzed in solution by means of 2 0 ' H NMR, 13C NMR, I R , UV, and dipole moment measurement techniques. Compound 1, CroHzvO $P, crystallized in the orthorhombic group P 2,2/2, u'ith Z = 4, a = 20.491( 2), b = 16.719(1), and c = 5.910(1). Compound 2, CZoH2903P, crystallized in the monoclinic space group P 2I with Z = 2, a = 9.266(1). b = 9.852(1), c = 10.954(1), and p = 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. I n solution, however, an anti arrangement of these two dipoles is slightly preferred.