THE DIMERIZATION OF (E)-1,3-DIPHENYL-1,3-BUTADIENE PROCEEDS SUPRAFACIALLY WITH RESPECT TO BOTH COMPONENTS - EVIDENCE FOR A CONCERTED [4+2]-CYCLOADDITION

被引：6

作者：

MULZER, J

MELZER, K

机构：

[1] Institut für Organische Chemie der Freien Universität, Berlin, D-14195

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 08期

关键词：

CYCLOADDITIONS; DIMERIZATIONS; DIRADICALS;

D O I：

10.1002/anie.199508951

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Despite the potential stabilization of diradical intermediates through the phenyl groups, the thermal dimerization of (E)‐1,3‐diphenyl‐1,3‐butadiene does not follow a diradical mechanism as previously assumed, but a concerted pathway. The case examined here is the dimerization of the deuteriated diene 1 giving 2, which proceeds suprafacially with regard to both diene and dienophile. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：895 / 898

页数：4

共 50 条

[1] TRANS-1-(DIMETHYLAMINO)-1,3-BUTADIENE - CONCERTED AND STEPWISE (4+2) CYCLOADDITIONS
SUSTMANN, R
ROGGE, M
NUCHTER, U
BANDMANN, H
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (07): : 1647 - 1656
[2] a(E)-1-methoxy-1,3-butadiene and 1,1-dimethoxy-1,3-butadiene in (4+2) cycloadditions. A mechanistic comparison
Sustmann, R
Tappanchai, S
Bandmann, H
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (50) : 12555 - 12561
[3] Cycloaddition of 1,3-benzothiazol-2-sulphenylchloride to (1E,3E)-1,4-diphenyl-1,3-butadiene
Borisov, AV
Nikonova, YA
Borisova, GN
Osmanov, VK
Matsulevich, Z
Zatonsky, GV
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2002, (06): : 855 - 856
[4] Cycloaddition of 1,3-Benzothiazole-2-sulfenyl Chloride to (1E,3E)-1,4-Diphenyl-1,3-butadiene
A. V. Borisov
Yu. A. Nikonova
G. N. Borisova
V. K. Osmanov
Zh. V. Matsulevich
G. V. Zatonskii
Chemistry of Heterocyclic Compounds, 2002, 38 (6) : 759 - 760
[5] [4+2] Cycloaddition of 1-phosphono-1,3-butadiene with azo- and nitroso-heterodienophiles
Monbaliu, Jean-Christophe
Marchand-Brynaert, Jacqueline
TETRAHEDRON LETTERS, 2008, 49 (11) : 1839 - 1842
[6] IRON-MEDIATED [4+2] CYCLOADDITION OF 1,3-BUTADIENE WITH ETHYNE AND PROPYNE IN THE GAS-PHASE
BAKHTIAR, R
DRADER, JJ
JACOBSON, DB
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) : 8304 - 8306
[7] Active space and basis set effects in CASPT2 models of the 1,3-butadiene-ethene cycloaddition and the 1,3-butadiene dimerization
Scarborough, David L. A.
Kobayashi, Rika
Thompson, Christopher D.
Izgorodina, Ekaterina I.
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2015, 115 (15) : 989 - 1001
[8] HIGH-PRESSURE (4+2) CYCLO-DIMERIZATION OF 2,3-DIMETHYL 1,3-BUTADIENE POSSIBLE COMPETITION BETWEEN CONCERTED AND STEPWISE MECHANISMS
JENNER, G
RIMMELIN, J
TETRAHEDRON LETTERS, 1980, 21 (32) : 3039 - 3042
[9] The first density functional study on the [4+2]-cycloaddition reactions of 1,2-diaza-1,3-butadiene with alkenes
Avalos, M
Babiano, R
Clemente, FR
Cintas, P
Gordillo, R
Jiménez, JL
Palacios, JC
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24): : 8251 - 8259
[10] Spectroscopic Characterization of Nonconcerted [4+2] Cycloaddition of 1,3-Butadiene with Lanthanacyclopropene To Form Lanthanum-Benzene in the Gas Phase
Hewage, Dilrukshi
Cao, Wenjin
Kim, Jong Hyun
Wang, Ya
Liu, Yang
Yang, Dong-Sheng
JOURNAL OF PHYSICAL CHEMISTRY A, 2017, 121 (06): : 1233 - 1239

← 1 2 3 4 5 →