Intramolecular four-membered ring rearrangements of 1-(N-benzyloxycarbonylamino)arylmethylphosphonate monoesters under electrospray ionization conditions

被引：10

作者：

Ma, Y ^{[1
]}

Liu, W ^{[1
]}

Zhao, WF ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China

来源：

INTERNATIONAL JOURNAL OF MASS SPECTROMETRY | 2006年 / 248卷 / 1-2期

关键词：

1-(N-Cbz-amino)arylmethylphosphonate monoesters; electrospray ionization; four-membered ring rearrangements;

D O I：

10.1016/j.ijms.2005.10.005

中图分类号：

O64 [物理化学（理论化学）、化学物理学]; O56 [分子物理学、原子物理学];

学科分类号：

070203 ; 070304 ; 081704 ; 1406 ;

摘要：

The mass spectrometric behavior of 1-[N-benzyloxycai-bonyl(Cbz)aminolarylmethylphosphonate monoesters was studied under positive ion electrospray ionization (ESI) conditions. The most interesting feature is that all title compounds predominantly undergo four-membered ring rearrangements to yield mainly nitrogen-containing fragment ions by loss of a carbon dioxide, phosphite, carbon dioxide plus phosphite, or benzyloxycarbonylphosphonate monoester. The fragmentation is obviously different from the corresponding 1-(N-Cbz-amino)arylmethylphosphonate diesters, which show a tendency to undergo an intramolecular six-membered ring benzyl rearrangement. (c) 2005 Elsevier B.V. All rights reserved.

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页码：17 / 20

页数：4

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