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Electron ionization mass spectra of phosphorus‐containing heterocycles. I. 1,4,4a,5,6,7,8,8a‐octahydro‐2 H ‐3,1,2‐benzoxazaphosphinine 2‐oxides
Author(s) -
Juhász Márta,
Martiskainen Olli,
Zalán Zita,
Fülöp Ferenc,
Pihlaja Kalevi
Publication year - 2006
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.2319
Subject(s) - chemistry , heteroatom , mass spectrum , fragmentation (computing) , ring (chemistry) , electron ionization , medicinal chemistry , alkene , bond cleavage , alkyl , ion , stereochemistry , ionization , crystallography , organic chemistry , catalysis , computer science , operating system
Abstract The electron ionization mass spectra of 27 cis ‐ and trans ‐annelated 1,4,4a,5,6,7,8,8a‐octahydro‐2 H ‐3,1,2‐benzoxazaphosphinine 2‐oxides were recorded to clarify the effects of the ring heteroatom (O or N), ring annelation, the P configuration and the substituents attached to the ring or to the N and P atoms. For compounds 1–12 different alkyl radical and alkene losses and the cleavage of the P–heteroatom bonds, instead of the P–C bonds, were representative and dependent mainly on the substitution on the N and P atoms. The replacement of Ph and OPh by N(CH 2 CH 2 Cl) 2 on the P atom had a dramatic influence on the fragmentation process: new fragment ions were obtained and very little M + . (1–3%) was formed. Only slight differences were found between some of the corresponding isomers, but interestingly the compounds formed clear groups on the basis of the differences in their fragmentation, depending on the ring‐N and ring‐P substituents. Copyright © 2006 John Wiley & Sons, Ltd.