ISSN:
0030-493X
Keywords:
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Homoadamantane derivatives can be divided into two groups according to their mass spectra. To the first group belong compounds with electron attracting substituents (COOH, CI, COOCH3, Br); compounds with electron releasing substituents (OCH3, OH, NH3, NHCOCH3) constitute the second group.The most characteristic feature of the first group compounds is the splitting off of the substituent. The hydrocarbon fragment [C11H17]+ thus formed then loses olefin molecules with the formation of corresponding ionic species C11-nH17-2n. The 3-substituted compounds of this group undergo thermal Wagner-Meerwein type rearrangements into adamantane derivatives, resulting in the [C10H15]+ (m/e 135) ion formation; this is the main difference between 1- and 3-substituted homoadamantanes.The series of [CnH2n-6X]+ ions (where X = OCH3, OH, NH2, NHCOCH3, n = 6 to 10) are characteristic of the mass spectra of the second group compounds, the ion [C6H6X]+, [M — C5H11]+ being the most abundant. The intensity ratio of [M — C5H11]+ to [M — C4H9]+ ions is 10:1 for 1-substituted and 3:1 for 3-substituted compounds of this group, allowing the location of the substituent. Some individual features of the spectra are also reported.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/oms.1210031108
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