Electronic effects in the electron ionization fragmentations of 2‐aryl substituted octahydro‐1,3‐ and ‐3,1‐benzoxazines

Pirjo Vainiotalo, Pirjo‐Liisa ‐L Lehtelä, F. Fülöp, G. Bernáth, Lauri Vuorilehto, Kalevi Pihlaja

Research output: Article

11 Citations (Scopus)

Abstract

The 70 eV electron ionization mass spectra of 27 2‐aryl substituted octahydro‐1,3‐ and ‐3,1‐benzoxazines have been recorded in order to find out how the site and stereochemistry of the ring fusion and especially the nature of the substitutent X on the 2‐phenyl group affect their fragmentation patterns. The structural isomers showed clearly different spectra; however, stereoisomeric differentiation was possible only with 1,3‐derivatives. The fragment‐ion peaks connected with the ionized ring and open chain forms of the compounds studied were clearly present in all the spectra. Analogously to the results obtained in solution, the electron‐withdrawing ability of X increased the abundance of the fragments originating from the ring form. Also, the relative importance of different fragmentation channels varied according to the electron donating or withdrawing ability of the substituent X.

Original languageEnglish
Pages (from-to)465-469
Number of pages5
JournalRapid Communications in Mass Spectrometry
Volume7
Issue number6
DOIs
Publication statusPublished - 1993

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Ionization
Stereochemistry
Electrons
Isomers
Fusion reactions

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry

Cite this

Electronic effects in the electron ionization fragmentations of 2‐aryl substituted octahydro‐1,3‐ and ‐3,1‐benzoxazines. / Vainiotalo, Pirjo; Lehtelä, Pirjo‐Liisa ‐L; Fülöp, F.; Bernáth, G.; Vuorilehto, Lauri; Pihlaja, Kalevi.

In: Rapid Communications in Mass Spectrometry, Vol. 7, No. 6, 1993, p. 465-469.

Research output: Article

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AU - Vainiotalo, Pirjo

AU - Lehtelä, Pirjo‐Liisa ‐L

AU - Fülöp, F.

AU - Bernáth, G.

AU - Vuorilehto, Lauri

AU - Pihlaja, Kalevi

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N2 - The 70 eV electron ionization mass spectra of 27 2‐aryl substituted octahydro‐1,3‐ and ‐3,1‐benzoxazines have been recorded in order to find out how the site and stereochemistry of the ring fusion and especially the nature of the substitutent X on the 2‐phenyl group affect their fragmentation patterns. The structural isomers showed clearly different spectra; however, stereoisomeric differentiation was possible only with 1,3‐derivatives. The fragment‐ion peaks connected with the ionized ring and open chain forms of the compounds studied were clearly present in all the spectra. Analogously to the results obtained in solution, the electron‐withdrawing ability of X increased the abundance of the fragments originating from the ring form. Also, the relative importance of different fragmentation channels varied according to the electron donating or withdrawing ability of the substituent X.

AB - The 70 eV electron ionization mass spectra of 27 2‐aryl substituted octahydro‐1,3‐ and ‐3,1‐benzoxazines have been recorded in order to find out how the site and stereochemistry of the ring fusion and especially the nature of the substitutent X on the 2‐phenyl group affect their fragmentation patterns. The structural isomers showed clearly different spectra; however, stereoisomeric differentiation was possible only with 1,3‐derivatives. The fragment‐ion peaks connected with the ionized ring and open chain forms of the compounds studied were clearly present in all the spectra. Analogously to the results obtained in solution, the electron‐withdrawing ability of X increased the abundance of the fragments originating from the ring form. Also, the relative importance of different fragmentation channels varied according to the electron donating or withdrawing ability of the substituent X.

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