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Strained heterocyclic systems. VII. The mass spectral fragmentations of dihydrocycloalka[ b ]quinolines and quinoline N ‐Oxides
Author(s) -
Koch Charles W.,
Milberb Richard M.,
Markgraf J. Hodge
Publication year - 1973
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570100616
Subject(s) - chemistry , quinoline , mass spectrum , ring (chemistry) , spectral line , molecule , ion , abundance (ecology) , high resolution , medicinal chemistry , crystallography , computational chemistry , organic chemistry , physics , remote sensing , astronomy , geology , fishery , biology
High resolution mass spectra of compounds 1‐6 were investigated. The quinolines ( 1‐3 ) all exhibit a prominent (M‐1) + peak and subsequent loss of HCN. These processes are consistent with azatropylium ion intermediates. The N ‐oxides ( 4‐6 ) all exhibit major peaks at (M‐16) + ; the abundance of the latter is related to the geometry of the molecule. The four‐membered ring compounds (3 and 6) give more complex spectra, which reflect the influence of the fused strained ring.