Thermal valence isomerization of 2,3-diborata-1,4-diphosphoniabuta-1,3-dienes to bicyclo[1.1.0]butanes and cyclobutane-1,3-diyls

被引:27
作者
Bourg, Jean-Baptiste
Rodriguez, Amor
Scheschkewitz, David
Gornitzka, Heinz
Bourissou, Didier
Bertrand, Guy
机构
[1] Univ Toulouse 3, Lab Heterochim Fondamentale & Appl, CNRS, UMR 5069, F-31062 Toulouse 9, France
[2] Univ Calif Riverside, UCR CNRS Joint Res Chem Lab, UMI 2957, Dept Chem, Riverside, CA 92521 USA
关键词
boron; butadienes; heterocycles; phosphorus; valence isomerization;
D O I
10.1002/anie.200701578
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Mind your Ps and Bs: Valence isomerizations of PBBP 1,3-butadienes are investigated and compared to those of PCCP and all-carbon systems. The 2,3-diborata-1,4-diphosphoniabuta-1,3-dienes thermally isomerize to bicyclo[1.1.0]butanes or cyclobutane-1,3-diyls. Under photolytic activation, the bicyclo[1.1.0]butanes rearrange into cyclobutenes. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5741 / 5745
页数:5
相关论文
共 78 条
[1]   Novel substituent effects on the mechanism of the thermal denitrogenation of 2,3-diazabicyclo[2.2.1]hept-2-ene derivatives, stepwise versus concerted [J].
Abe, M ;
Ishihara, C ;
Kawanami, S ;
Masuyama, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :10-11
[2]   2-silyl group effect on the reactivity of cyclopentane-1,3-diyls. Intramolecular ring-closure versus silyl migration [J].
Abe, M ;
Kawanami, S ;
Ishihara, C ;
Nojima, M .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5622-5626
[3]   Effects of spiroconjugation on the calculated singlet-triplet energy gap in 2,2-dialkoxycyclopentane-1,3-diyls and on the experimental electronic absorption spectra of singlet 1,3-diphenyl derivatives. assignment of the lowest-energy electronic transition of singlet cyclopentane-1,3-diyls [J].
Abe, M ;
Adam, W ;
Borden, WT ;
Hattori, M ;
Hrovat, DA ;
Nojima, M ;
Nozaki, K ;
Wirz, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) :574-582
[4]  
Abe M., 2006, ANGEW CHEM, V118, P7992
[5]   An extremely long-lived singlet 4,4-dimethoxy-3,5-diphenylpyrazolidine-3,5-diyl derivative: A notable nitrogen-atom effect on intra- and intermolecular reactivity [J].
Abe, Manabu ;
Kubo, Emi ;
Nozaki, Koichi ;
Matsuo, Takashi ;
Hayashi, Takashi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (46) :7828-7831
[6]   New development of reactive intermediate chemistry: A case study of singlet biradicals [J].
Abe, Manabu .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2007, 65 (01) :14-20
[7]   Experimental probe for hyperconjugative resonance contribution in stabilizing the singlet state of 2,2-dialkoxy-1,3-diyls: Regioselective 1,2-oxygen migration [J].
Abe, Manabu ;
Hattori, Masanori ;
Takegami, Akinobu ;
Masuyama, Araki ;
Hayashi, Takashi ;
Seki, Shu ;
Tagawa, Seiichi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (24) :8008-8014
[8]  
AFARIN M, 1996, MAIN GROUP CHEM, V1, P197
[9]   Radical-type reactivity of the 1,3-dibora-2,4-diphosphoniocyclobutane-1,3-diyl [J].
Amii, H ;
Vranicar, L ;
Gornitzka, H ;
Bourissou, D ;
Bertrand, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (05) :1344-1345
[10]  
[Anonymous], ORGANOSILICON CHEM