Gas-phase polar cycloadditions

被引:36
作者
Eberlin, MN [1 ]
机构
[1] Univ Estadual Campinas, UNICAMP, Inst Chem, Thomson Mass Spectrometry Lab, BR-13083970 Campinas, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
cycloaddition reactions; pericyclic reactions; mass spectrometry; structure selective gas-phase ion/molecule reactions; reaction mechanisms;
D O I
10.1016/j.ijms.2004.05.002
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 dilute gas-phase environment of mass spectrometers provides versatile and convenient medium in which chemists can form a great variety of ionic species and study their intrinsic reactivity exploring reaction mechanisms and screening for new reactions and their applications. Recent and illustrative examples of gas-phase polar cycloadditions of even and odd-electrons ions, which have been observed (some for the first time) in the solvent- and counter ion-free environment of mass spectrometers, are presented. Synthetic and analytical applications of such reactions and correlations with analogous reactions observed in solution are also discussed. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:263 / 278
页数:16
相关论文
共 85 条
[1]  
[Anonymous], COMP CHEM TERM
[2]   The simplest azabutadienes in their N-protonated forms. Generation, stability, and cycloaddition-reactivity in the gas phase [J].
Augusti, R ;
Gozzo, FC ;
Moraes, LAB ;
Sparrapan, R ;
Eberlin, MN .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) :4889-4897
[3]   IRON-MEDIATED [4+2] CYCLOADDITION OF 1,3-BUTADIENE WITH ETHYNE AND PROPYNE IN THE GAS-PHASE [J].
BAKHTIAR, R ;
DRADER, JJ ;
JACOBSON, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8304-8306
[4]   CATION RADICAL PERICYCLIC-REACTIONS [J].
BAULD, NL ;
BELLVILLE, DJ ;
HARIRCHIAN, B ;
LORENZ, KT ;
PABON, RA ;
REYNOLDS, DW ;
WIRTH, DD ;
CHIOU, HS ;
MARSH, BK .
ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (10) :371-378
[5]   [4+2(+)] DIELS-ALDER CYCLOADDITION TO C-60 AND C-70 RADICAL CATIONS IN THE GAS-PHASE - A COMPARISON WITH SOLUTION [J].
BECKER, H ;
JAVAHERY, G ;
PETRIE, S ;
BOHME, DK .
JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (22) :5591-5592
[6]  
Bernardi F, 2000, CHEM-EUR J, V6, P537, DOI 10.1002/(SICI)1521-3765(20000204)6:3<537::AID-CHEM537>3.0.CO
[7]  
2-I
[8]  
BOGER DL, 1987, HETERO DIELSALDER ME
[9]   CYCLOADDITION REACTIONS BETWEEN 1,3-BUTADIENE RADICAL CATIONS AND ETHENE IN THE GAS-PHASE [J].
BOUCHOUX, G ;
SALPIN, JY .
RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 1994, 8 (04) :325-328
[10]   Condensation reactions between 1,3-butadiene radical cation and acetylene in the gas phase [J].
Bouchoux, G ;
Nguyen, MT ;
Salpin, JY .
JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (24) :5778-5786