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Mass spectrometry of homoadamantane derivatives
Author(s) -
Yurchenko A. G.,
Stepanov F. N.,
Isaeva S. S.,
Zolotarev B. M.,
Kadentsev V. I.,
Chizhov O. S.
Publication year - 1970
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210031108
Subject(s) - substituent , chemistry , mass spectrum , ion , olefin fiber , molecule , stereochemistry , group (periodic table) , crystallography , medicinal chemistry , ionic bonding , mass spectrometry , organic chemistry , catalysis , chromatography
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, COOCH 3 , Br); compounds with electron releasing substituents (OCH 3 , OH, NH 3 , NHCOCH 3 ) constitute the second group. The most characteristic feature of the first group compounds is the splitting off of the substituent. The hydrocarbon fragment [C 11 H 17 ] + thus formed then loses olefin molecules with the formation of corresponding ionic species C 11−n H 17−2n . The 3‐substituted compounds of this group undergo thermal Wagner‐Meerwein type rearrangements into adamantane derivatives, resulting in the [C 10 H 15 ] + ( m / e 135) ion formation; this is the main difference between 1‐ and 3‐substituted homoadamantanes. The series of [C n H 2n−6 X] + ions (where X = OCH 3 , OH, NH 2 , NHCOCH 3 , n = 6 to 10) are characteristic of the mass spectra of the second group compounds, the ion [C 6 H 6 X] + , [M C 5 H 11 ] + being the most abundant. The intensity ratio of [M C 5 H 11 ] + to [M C 4 H 9 ] + 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.