Novel Ortho effects detected in the fast atom bombardment mass spectra of substituted bisaryl phosphate antagonists of platelet-activating factor
✍ Scribed by Marshall M. Siegel; Rushung Tsao; Allan Wissner
- Publisher
- John Wiley and Sons
- Year
- 1993
- Tongue
- English
- Weight
- 878 KB
- Volume
- 28
- Category
- Article
- ISSN
- 1076-5174
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✦ Synopsis
A series of substituted bisaryl phosphate compounds, (RICH,)+ ArOP = 0(0-)(OArR2R3), was analyzed and characterized by fast atom bombardment mass spectrometry. Abundant fragment ions were observed and correlated with the proposed structures. From fragmentation patterns, 'ortho effect' reactions were demonstrated to have occurred when the phosphoryl oxygen reacted with the (CH,R')+ and C=O(OCH,) substituents in the ortho position, relative to the phosphate group, and displaced the R' and OCH, groups, respectively, to produce phosphorus containing six-membered rings fused to the aryl moiety. When the (CH,R')+ substituents were in the meta position relative to the phosphate group, the 'ortho effect' reactions were not observed. However, when the C=O(OCH,) substituent was in the meta position relative to the phosphate group, an abundant fragment ion containing a five-membered phosphate ring fused to the aryl ring was detected with the original phosphoryl oxygen ortho to both the phosphate oxygen and a formyl group, formed from the original C=O(OCH,) substituent. All other fragmentations not involving the 'ortho effect' reactions were nearly identical for the different structural isomers of the substituted bisaryl phosphate compounds.