Mass Spectrometric Fragmentation of 1,8-Bis[4-substituted-(oxazolin-2-yl)] anthracenes: Ring-contraction Rearrangement of Oxazoline Ring under Electron-Impact Ionization Conditions

Chemical Research in Chinese Universities ›› 2006, Vol. 22 ›› Issue (6): 753-755.doi:

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Mass Spectrometric Fragmentation of 1,8-Bis[4-substituted-(oxazolin-2-yl)] anthracenes: Ring-contraction Rearrangement of Oxazoline Ring under Electron-Impact Ionization Conditions

JIAO Peng, MA Lin-ge, ZHANG Qi-han and XU Jia-xi

Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China

Received:2005-10-21 Revised:1900-01-01 Online:2006-11-25 Published:2006-11-25
Contact: XU Jia-xi E-mail:jxxu@pku.edu.cn

Abstract

Abstract: The mass spectrometric fragmentation of 1,8-bis[4-substituted(oxazolin-2-yl)] anthracenes(AnBOXes) was investigated by using mass-analyzed ion kinetic energy spectrometry under electron-impact ionization conditions. All the compounds could undergo a ring contraction by the loss of an RCH—CH₂ molecule to form 1-oxazirinyl-8-(oxazolin-2-yl) anthracene ions, which could further lose an R radical, followed by the loss of oxazoline. These ions could also eliminate an R radical and subsequently undergo ring-contraction rearrangements to lose a CHCH₂O fragment and an epoxide molecule, respectively. The ions that are formed could further lose CHCH₂O and CH₂==CH fragments. Se-veral ring-contraction rearrangements of the oxazoline ring were observed under electron-impact ionization conditions.

Key words: Bis-oxazoline, EI-MS, Fragmentation, Ring contraction, Bis-oxazoline, EI-MS, Fragmentation, Ring contraction

JIAO Peng, MA Lin-ge, ZHANG Qi-han , XU Jia-xi . Mass Spectrometric Fragmentation of 1,8-Bis[4-substituted-(oxazolin-2-yl)] anthracenes: Ring-contraction Rearrangement of Oxazoline Ring under Electron-Impact Ionization Conditions[J]. Chemical Research in Chinese Universities, 2006, 22(6): 753-755.

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Mass Spectrometric Fragmentation of 1,8-Bis[4-substituted-(oxazolin-2-yl)] anthracenes: Ring-contraction Rearrangement of Oxazoline Ring under Electron-Impact Ionization Conditions

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