Electron ionization mass spectra of phosphorus-containing heterocycles. I. 1,4,4a,5,6,7,8,8a-octahydro-2H-3,1,2-benzoxazaphosphinine 2-oxides
The electron ionization mass spectra of 27 cis‐ and trans‐annelated 1,4,4a,5,6,7,8,8a‐octahydro‐2H‐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...
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| Published in | Rapid communications in mass spectrometry Vol. 20; no. 3; pp. 433 - 437 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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Chichester, UK
John Wiley & Sons, Ltd
01.01.2006
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| Abstract | The electron ionization mass spectra of 27 cis‐ and trans‐annelated 1,4,4a,5,6,7,8,8a‐octahydro‐2H‐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(CH2CH2Cl)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. |
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| AbstractList | The electron ionization mass spectra of 27 cis- and trans-annelated 1,4,4a,5,6,7,8,8a-octahydro-2H-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(CH2CH2Cl)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. The electron ionization mass spectra of 27 cis‐ and trans‐annelated 1,4,4a,5,6,7,8,8a‐octahydro‐2H‐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(CH2CH2Cl)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. The electron ionization mass spectra of 27 cis- and trans-annelated 1,4,4a,5,6,7,8,8a-octahydro-2H-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(CH2CH2Cl)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.The electron ionization mass spectra of 27 cis- and trans-annelated 1,4,4a,5,6,7,8,8a-octahydro-2H-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(CH2CH2Cl)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. |
| Author | Zalán, Zita Martiskainen, Olli Juhász, Márta Pihlaja, Kalevi Fülöp, Ferenc |
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| References | (b) Jalonen J, Pihlaja K. Org. Mass Spectrom. 1973; 7: 1203, and references cited therein Verkade JG. Phosphorus, Sulfur, Silicon Relat. Elem. 1976; 2: 251. Zielińska B, Stec WJ. Org. Mass Spectrom. 1978; 13: 65. (d) Winkler J, Grützmacher HF. Org. Mass Spectrom. 1970; 3: 1139. Busker E, Koberstein E, Niemeyer U, Engel J, Linscheid M. Biomed. Environ. Mass Spectrom. 1988; 15: 163. Hudson RF, Verkade JG. Tetrahedron Lett. 1975; 16: 3231, and references cited therein. Murai A, Kainosho M. Org. Mass Spectrom. 1976; 11: 175. Jakobsen P, Treppendahl S, Wieczorkowski J. Org. Mass Spectrom. 1972; 6: 1303. Kivelä H, Zalán Z, Tähtinen P, Sillanpää R, Fülöp F, Pihlaja K. Eur. J. Org. Chem. 2005; 1189. Przybylski M, Ringsdorf H, Lenssen U, Peter G, Voelcker G, Wagner T, Hohorst HJ. Biomed. Mass Spectrom. 1977; 4: 209. Francis GW, Tjessem K, Dale A, Gramstad T. Acta Chem. Scand. Ser. B 1976; 30: 31. Phillips LR, Zon G, Bone WM, Boyd VL, Ludeman SM. Org. Mass Spectrom. 1989; 24: 347. (b) Williams DH, Beynon JH. Org. Mass Spectrom. 1976; 11: 103. Viljanen T, Tähtinen P, Pihlaja K, Fülöp F. J. Org. Chem. 1998; 63: 618. Kenttämaa HI, Savolahti P, Koskikallio J. Int. J. Mass Spectrom. Ion Phys. 1983; 47: 463. Mruzek MN, Shaw IC. Biomed. Mass Spectrom. 1984; 11: 360. Kulkarni PS, Gogte VN, Modak AS, Sahasrabudhe SD, Tilak BD. Org. Mass Spectrom. 1983; 18: 489. (a) McLafferty FW. Interpretation of Mass Spectra. Benjamin: New York, 1973 (c) Green MM, Cook RJ, Schwab JM, Roy RB. J. Am. Chem. Soc. 1970; 92: 3076 See, for example: (a) Meyerson S, Weitkamp AW. Org. Mass Spectrom. 1968; 1: 659, and references cited therein 1976; 30 1968 1973 1970 1970; 1 7 92 3 1976; 11 1984; 11 1988; 15 1975; 16 1976; 2 1977; 4 2005 1978; 13 1973 1976; 11 1998; 63 1983; 18 1989; 24 1972; 6 1983; 47 |
| References_xml | – reference: Mruzek MN, Shaw IC. Biomed. Mass Spectrom. 1984; 11: 360. – reference: (c) Green MM, Cook RJ, Schwab JM, Roy RB. J. Am. Chem. Soc. 1970; 92: 3076; – reference: Murai A, Kainosho M. Org. Mass Spectrom. 1976; 11: 175. – reference: Hudson RF, Verkade JG. Tetrahedron Lett. 1975; 16: 3231, and references cited therein. – reference: See, for example: (a) Meyerson S, Weitkamp AW. Org. Mass Spectrom. 1968; 1: 659, and references cited therein; – reference: Busker E, Koberstein E, Niemeyer U, Engel J, Linscheid M. Biomed. Environ. Mass Spectrom. 1988; 15: 163. – reference: Kivelä H, Zalán Z, Tähtinen P, Sillanpää R, Fülöp F, Pihlaja K. Eur. J. Org. Chem. 2005; 1189. – reference: Przybylski M, Ringsdorf H, Lenssen U, Peter G, Voelcker G, Wagner T, Hohorst HJ. Biomed. Mass Spectrom. 1977; 4: 209. – reference: Jakobsen P, Treppendahl S, Wieczorkowski J. Org. Mass Spectrom. 1972; 6: 1303. – reference: Zielińska B, Stec WJ. Org. Mass Spectrom. 1978; 13: 65. – reference: (b) Williams DH, Beynon JH. Org. Mass Spectrom. 1976; 11: 103. – reference: (a) McLafferty FW. Interpretation of Mass Spectra. Benjamin: New York, 1973; – reference: Francis GW, Tjessem K, Dale A, Gramstad T. Acta Chem. Scand. Ser. B 1976; 30: 31. – reference: Phillips LR, Zon G, Bone WM, Boyd VL, Ludeman SM. Org. Mass Spectrom. 1989; 24: 347. – reference: Verkade JG. Phosphorus, Sulfur, Silicon Relat. Elem. 1976; 2: 251. – reference: (b) Jalonen J, Pihlaja K. Org. Mass Spectrom. 1973; 7: 1203, and references cited therein; – reference: (d) Winkler J, Grützmacher HF. Org. Mass Spectrom. 1970; 3: 1139. – reference: Kenttämaa HI, Savolahti P, Koskikallio J. Int. J. Mass Spectrom. Ion Phys. 1983; 47: 463. – reference: Kulkarni PS, Gogte VN, Modak AS, Sahasrabudhe SD, Tilak BD. Org. Mass Spectrom. 1983; 18: 489. – reference: Viljanen T, Tähtinen P, Pihlaja K, Fülöp F. J. Org. Chem. 1998; 63: 618. – volume: 6 start-page: 1303 year: 1972 publication-title: Org. Mass Spectrom. – volume: 15 start-page: 163 year: 1988 publication-title: Biomed. Environ. Mass Spectrom. – volume: 13 start-page: 65 year: 1978 publication-title: Org. Mass Spectrom. – volume: 1 7 92 3 start-page: 659 1203 3076 1139 year: 1968 1973 1970 1970 publication-title: Org. Mass Spectrom. Org. Mass Spectrom. J. Am. Chem. Soc. Org. Mass Spectrom. – volume: 11 start-page: 175 year: 1976 publication-title: Org. Mass Spectrom. – start-page: 1189 year: 2005 publication-title: Eur. J. Org. Chem. – volume: 11 start-page: 103 year: 1973 1976 publication-title: Org. Mass Spectrom. – volume: 63 start-page: 618 year: 1998 publication-title: J. Org. Chem. – volume: 24 start-page: 347 year: 1989 publication-title: Org. Mass Spectrom. – volume: 30 start-page: 31 year: 1976 publication-title: Acta Chem. Scand. Ser. B – volume: 47 start-page: 463 year: 1983 publication-title: Int. J. Mass Spectrom. Ion Phys. – volume: 18 start-page: 489 year: 1983 publication-title: Org. Mass Spectrom. – volume: 16 start-page: 3231 year: 1975 publication-title: Tetrahedron Lett. – volume: 11 start-page: 360 year: 1984 publication-title: Biomed. Mass Spectrom. – volume: 2 start-page: 251 year: 1976 publication-title: Phosphorus, Sulfur, Silicon Relat. Elem. – volume: 4 start-page: 209 year: 1977 publication-title: Biomed. Mass Spectrom. |
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| Snippet | The electron ionization mass spectra of 27 cis‐ and trans‐annelated 1,4,4a,5,6,7,8,8a‐octahydro‐2H‐3,1,2‐benzoxazaphosphinine 2‐oxides were recorded to clarify... The electron ionization mass spectra of 27 cis- and trans-annelated 1,4,4a,5,6,7,8,8a-octahydro-2H-3,1,2-benzoxazaphosphinine 2-oxides were recorded to clarify... |
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| Title | Electron ionization mass spectra of phosphorus-containing heterocycles. I. 1,4,4a,5,6,7,8,8a-octahydro-2H-3,1,2-benzoxazaphosphinine 2-oxides |
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