Electron ionization mass spectra of phosphorus-containing heterocycles. II. 1,2,3,4,4a,5,6,7,8,8a-decahydro-1,3,2-benzodiazaphosphinine 2-oxides

Olli Martiskainen, Márta Juhász, Zita Zalán, F. Fülöp, Kalevi Pihlaja

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The electron ionization mass spectra of cis- and trans-fused 1,2,3,4,4a,5,6,7,8,8a-decahydro-1,3, 2-benzodiazaphosphinine 2-oxides (1-17) were recorded, and the fragmentation pathways were established and compared with those of 1,4,4a,5,6,7,8,8a-octahydro-2H-3,1,2-benzoxazaphosphinine 2-oxides. In general, the mass spectral behaviors of the isomeric compounds were very similar and it was mostly impossible to differentiate them from each other on the basis of the relative abundances of their characteristic fragment ions. The compounds in which R2 = Ph or OPh exhibited a series of common fragments, e.g. [R2H]+, R2PONHR 1(3)+, [M-C3H7]+ and [M-C 4H9]+, the latter two ions being present in the spectra of only two of the derivatives with an N(CH2CH 2Cl)2 substituent on the P atom. When R2 = Ph, numerous other alkyl radicals, alkenes and a cycloalkane were also ejected and these compounds also lost NH2, NH3, CH3N, CH4N or CH3NH2. The compounds with an N(CH 2CH2Cl)2 substituent on the P atom most closely resembled their 3,1,2-O,N,P analogs in respect of the dominant role of this substituent.

Original languageEnglish
Pages (from-to)1621-1627
Number of pages7
JournalRapid Communications in Mass Spectrometry
Volume20
Issue number11
DOIs
Publication statusPublished - 2006

Fingerprint

Phosphorus
Oxides
Ionization
Cycloparaffins
Ions
Atoms
Electrons
Alkenes
Derivatives

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy

Cite this

Electron ionization mass spectra of phosphorus-containing heterocycles. II. 1,2,3,4,4a,5,6,7,8,8a-decahydro-1,3,2-benzodiazaphosphinine 2-oxides. / Martiskainen, Olli; Juhász, Márta; Zalán, Zita; Fülöp, F.; Pihlaja, Kalevi.

In: Rapid Communications in Mass Spectrometry, Vol. 20, No. 11, 2006, p. 1621-1627.

Research output: Contribution to journalArticle

@article{e7256baf57324d0f892e6c0806d87a0d,
title = "Electron ionization mass spectra of phosphorus-containing heterocycles. II. 1,2,3,4,4a,5,6,7,8,8a-decahydro-1,3,2-benzodiazaphosphinine 2-oxides",
abstract = "The electron ionization mass spectra of cis- and trans-fused 1,2,3,4,4a,5,6,7,8,8a-decahydro-1,3, 2-benzodiazaphosphinine 2-oxides (1-17) were recorded, and the fragmentation pathways were established and compared with those of 1,4,4a,5,6,7,8,8a-octahydro-2H-3,1,2-benzoxazaphosphinine 2-oxides. In general, the mass spectral behaviors of the isomeric compounds were very similar and it was mostly impossible to differentiate them from each other on the basis of the relative abundances of their characteristic fragment ions. The compounds in which R2 = Ph or OPh exhibited a series of common fragments, e.g. [R2H]+, R2PONHR 1(3)+, [M-C3H7]+ and [M-C 4H9]+, the latter two ions being present in the spectra of only two of the derivatives with an N(CH2CH 2Cl)2 substituent on the P atom. When R2 = Ph, numerous other alkyl radicals, alkenes and a cycloalkane were also ejected and these compounds also lost NH2, NH3, CH3N, CH4N or CH3NH2. The compounds with an N(CH 2CH2Cl)2 substituent on the P atom most closely resembled their 3,1,2-O,N,P analogs in respect of the dominant role of this substituent.",
author = "Olli Martiskainen and M{\'a}rta Juh{\'a}sz and Zita Zal{\'a}n and F. F{\"u}l{\"o}p and Kalevi Pihlaja",
year = "2006",
doi = "10.1002/rcm.2481",
language = "English",
volume = "20",
pages = "1621--1627",
journal = "Rapid Communications in Mass Spectrometry",
issn = "0951-4198",
publisher = "John Wiley and Sons Ltd",
number = "11",

}

TY - JOUR

T1 - Electron ionization mass spectra of phosphorus-containing heterocycles. II. 1,2,3,4,4a,5,6,7,8,8a-decahydro-1,3,2-benzodiazaphosphinine 2-oxides

AU - Martiskainen, Olli

AU - Juhász, Márta

AU - Zalán, Zita

AU - Fülöp, F.

AU - Pihlaja, Kalevi

PY - 2006

Y1 - 2006

N2 - The electron ionization mass spectra of cis- and trans-fused 1,2,3,4,4a,5,6,7,8,8a-decahydro-1,3, 2-benzodiazaphosphinine 2-oxides (1-17) were recorded, and the fragmentation pathways were established and compared with those of 1,4,4a,5,6,7,8,8a-octahydro-2H-3,1,2-benzoxazaphosphinine 2-oxides. In general, the mass spectral behaviors of the isomeric compounds were very similar and it was mostly impossible to differentiate them from each other on the basis of the relative abundances of their characteristic fragment ions. The compounds in which R2 = Ph or OPh exhibited a series of common fragments, e.g. [R2H]+, R2PONHR 1(3)+, [M-C3H7]+ and [M-C 4H9]+, the latter two ions being present in the spectra of only two of the derivatives with an N(CH2CH 2Cl)2 substituent on the P atom. When R2 = Ph, numerous other alkyl radicals, alkenes and a cycloalkane were also ejected and these compounds also lost NH2, NH3, CH3N, CH4N or CH3NH2. The compounds with an N(CH 2CH2Cl)2 substituent on the P atom most closely resembled their 3,1,2-O,N,P analogs in respect of the dominant role of this substituent.

AB - The electron ionization mass spectra of cis- and trans-fused 1,2,3,4,4a,5,6,7,8,8a-decahydro-1,3, 2-benzodiazaphosphinine 2-oxides (1-17) were recorded, and the fragmentation pathways were established and compared with those of 1,4,4a,5,6,7,8,8a-octahydro-2H-3,1,2-benzoxazaphosphinine 2-oxides. In general, the mass spectral behaviors of the isomeric compounds were very similar and it was mostly impossible to differentiate them from each other on the basis of the relative abundances of their characteristic fragment ions. The compounds in which R2 = Ph or OPh exhibited a series of common fragments, e.g. [R2H]+, R2PONHR 1(3)+, [M-C3H7]+ and [M-C 4H9]+, the latter two ions being present in the spectra of only two of the derivatives with an N(CH2CH 2Cl)2 substituent on the P atom. When R2 = Ph, numerous other alkyl radicals, alkenes and a cycloalkane were also ejected and these compounds also lost NH2, NH3, CH3N, CH4N or CH3NH2. The compounds with an N(CH 2CH2Cl)2 substituent on the P atom most closely resembled their 3,1,2-O,N,P analogs in respect of the dominant role of this substituent.

UR - http://www.scopus.com/inward/record.url?scp=33646938049&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33646938049&partnerID=8YFLogxK

U2 - 10.1002/rcm.2481

DO - 10.1002/rcm.2481

M3 - Article

C2 - 16637001

AN - SCOPUS:33646938049

VL - 20

SP - 1621

EP - 1627

JO - Rapid Communications in Mass Spectrometry

JF - Rapid Communications in Mass Spectrometry

SN - 0951-4198

IS - 11

ER -