Radical-type reactivity of the 1,3-dibora-2,4-diphosphoniocyclobutane-1,3-diyl

被引:76
作者
Amii, H
Vranicar, L
Gornitzka, H
Bourissou, D
Bertrand, G
机构
[1] Univ Toulouse 3, CNRS, UMR 5069, Lab Heterochim Fondamentale & Appl, F-31062 Toulouse 04, France
[2] Univ Calif Riverside, Dept Chem, CNRS, UMR 2282,Joint Res Chem Lab, Riverside, CA 92521 USA
关键词
D O I
10.1021/ja039920i
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Despite through-space and through-bond B-B interactions, the stable 1,3-bora-2,4-diphosphoniocyclobutane-1,3-diyl displays some radical-type behavior, as illustrated by the spontaneous formation of the trans 1,3-adduct with trimethyltin hydride and a B-spiro derivative with bromotrichloromethane. Copyright © 2004 American Chemical Society.
引用
收藏
页码:1344 / 1345
页数:2
相关论文
共 25 条
[1]   Mechanism of an alcohol-trapping reaction in the direct and benzophenone-sensitized photodenitrogenation of a spiroepoxy-substituted azoalkane: Solvent effects and stereochemical deuterium labeling [J].
Abe, M ;
Adam, W ;
Minamoto, T ;
Ino, Y ;
Nojima, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1796-1803
[2]   DFT prediction of ground-state spin multiplicity of cyclobutane-1,3-diyls: Notable effects of two sets of through-bond interactions [J].
Abe, M ;
Ishihara, C ;
Nojima, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1618-1621
[3]   On the electronic character of localized singlet 2,2-dimethoxycyclopentane-1,3-diyl diradicals: Substituent effects on the lifetime [J].
Abe, M ;
Adam, W ;
Hara, M ;
Hattori, M ;
Majima, T ;
Nojima, M ;
Tachibana, K ;
Tojo, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) :6540-6541
[4]   Photochemical generation and methanol trapping of localized 1,3 and 1,4 singlet diradicals derived from a spiroepoxy-substituted cyclopentane-1,3-diyl [J].
Abe, M ;
Adam, W ;
Nau, WM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (44) :11304-11310
[5]   Intramolecular and intermolecular reactivity of localized singlet diradicals: The exceedingly long-lived 2,2-diethoxy-1,3-diphenylcyclopentane-1,3-diyl [J].
Abe, M ;
Adam, W ;
Heidenfelder, T ;
Nau, WM ;
Zhang, XY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (09) :2019-2026
[6]   Transient spectroscopy of a derivative of 2,2-difluoro-1,3-diphenylcyclopentane-1,3-diyl - A persistent localized singlet 1,3-diradical [J].
Adam, W ;
Borden, WT ;
Burda, C ;
Foster, H ;
Heidenfelder, T ;
Heubes, M ;
Hrovat, DA ;
Kita, F ;
Lewis, SB ;
Scheutzow, D ;
Wirz, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (03) :593-594
[7]  
[Anonymous], ENZYCLOPEDIA COMPUTA
[8]   B2P2 rings:: through-space π bond or stable diradical?: A theoretical study [J].
Cheng, MJ ;
Hu, CH .
MOLECULAR PHYSICS, 2003, 101 (09) :1319-1323
[9]   1,3-DIBORA-[3]FERROCENOPHANES - SYNTHESIS AND CHARACTERIZATION [J].
HERBERHOLD, M ;
DORFLER, U ;
MILIUS, W ;
WRACKMEYER, B .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 492 (01) :59-63
[10]   How diradicaloid is a stable diradical? [J].
Jung, YS ;
Head-Gordon, M .
CHEMPHYSCHEM, 2003, 4 (05) :522-525