1980
DOI: 10.1002/oms.1210150313
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Stereochemical effects in the mass spectra of 2‐hydroxy‐, 5‐hydroxy‐ and 2,5‐dihydroxyprotoadamantanes

Abstract: Electron ionization and methane and isobutane chemical ionization mass spectra have been obtained for the four configurationally isomeric 2,5-protoadamantanediols and the corresponding model monoalcohols. Although the electron impact (both 70 and 15 eV) and methane chemical ionization mass spectra of the 2,5-protoadamantanediols are distinct, the variations are not large and in general they are difficult to rationalize in terms of specific structural features. In contrast, the isobutane chemical ionization mas… Show more

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Cited by 17 publications
(6 citation statements)
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“…At 60°, the ratios 15l5 and 11l1 (% Z 60) for the ( M -H)+ ions are found for the 5b cisltrans and the 11 endolexo pairs, respectively. The steric shielding control in 5b and 11, which is cancelled in l l a and l l b by additional methyl shielding of the exo H (a)-atoms, is in agreement with previous observations on 11 [43] and epimeric protoadamantols [44]. Thus, steric shielding next to steric compression, is a second useful stereochemical concept in CI.…”
Section: T ( M -H)+ ( M -Oh)+ Mlz 83 (M-h)+ (M-oh)+ (M-h20)' (M-h-hsupporting
confidence: 90%
“…At 60°, the ratios 15l5 and 11l1 (% Z 60) for the ( M -H)+ ions are found for the 5b cisltrans and the 11 endolexo pairs, respectively. The steric shielding control in 5b and 11, which is cancelled in l l a and l l b by additional methyl shielding of the exo H (a)-atoms, is in agreement with previous observations on 11 [43] and epimeric protoadamantols [44]. Thus, steric shielding next to steric compression, is a second useful stereochemical concept in CI.…”
Section: T ( M -H)+ ( M -Oh)+ Mlz 83 (M-h)+ (M-oh)+ (M-h20)' (M-h-hsupporting
confidence: 90%
“…But, since these spectra contain essentially no fragmentation they usually provide no structural information. A few special cases have been reported in which the Cl reagent ions react selectively with a particular functional group or combination of functionalities (8)(9)(10)(11). These spectra can provide information about specific structural features of the sample substrate, but interpretation requires some prior knowledge of the sample.…”
Section: Acknowledgmentmentioning
confidence: 99%
“…Analysis of stereoisomers is usually carried out by other MS techniques,1, 2 and examples of these techniques being used to discriminate between enantiomers or diastereoisomers have been reported for a variety of classes of organic substances 3–13. There are only a limited number of studies presenting differences in the EI mass spectra of diastereoisomers in saturated six‐membered ring derivatives 14–16…”
mentioning
confidence: 99%