On the origin of the alternating Diels-Alder reactivity in [n]dendralenes

被引：24

作者：

Paddon-Row, Michael N. ^{[1
]}

Sherburn, Michael S. ^{[2
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

[2] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 06期

基金：

澳大利亚研究理事会;

关键词：

PRACTICAL SYNTHESIS; DENDRALENE FAMILY; DIMERIZATION; HYDROCARBONS; BUTADIENE; CHEMISTRY; BONDS;

D O I：

10.1039/c1cc15455a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

G4(MP2) calculations on Diels-Alder reactions of [3]- and [4]dendralene have revealed that reactant dendralene conformer populations and closed-shell singlet bis-pericyclic transition states explain their different reactivities.

引用

页码：832 / 834

页数：3

共 20 条

[11] NEW SYNTHESIS OF METHYL 1,3-BUTADIENE-2-CARBOXYLATE BY THE CHELETROPIC EXTRUSION OF CARBON-MONOXIDE FROM 3-CARBOMETHOXY-3,4-PENTADIENAL AND A STUDY OF ITS DIMERIZATION TO GIVE DIMETHYL MIKANECATE (DIMETHYL 4-ETHENYL-1-CYCLOHEXENE-1,4-DICARBOXYLATE)
JUNG, ME
ZIMMERMAN, CN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) : 7813 - 7814
[12] FACIAL SELECTIVITIES AND RATE EFFECTS IN THE THERMAL [4 + 2] DIMERIZATION OF ARYLATED 1,3-DIENES 1,5-H SHIFT VERSUS DIMERIZATION OF (Z)-1,3-DIENES
MULZER, J
KUHL, U
HUTTNER, G
EVERTZ, K
[J]. CHEMISCHE BERICHTE, 1988, 121 (12) : 2231 - 2238
[13] THE DIMERIZATION OF (E)-1,3-DIPHENYL-1,3-BUTADIENE PROCEEDS SUPRAFACIALLY WITH RESPECT TO BOTH COMPONENTS - EVIDENCE FOR A CONCERTED [4+2]-CYCLOADDITION
MULZER, J
MELZER, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (08): : 895 - 898
[14] SOME ASPECTS OF ORBITAL INTERACTIONS THROUGH BONDS - PHYSICAL AND CHEMICAL CONSEQUENCES
PADDONROW, MN
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (08) : 245 - 251
[15] Practical synthesis and Diels-Alder chemistry of [4]dendralene
Payne, AD
Willis, AC
Sherburn, MS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) : 12188 - 12189
[16] Practical Synthesis of the Dendralene Family Reveals Alternation in Behavior
Payne, Alan D.
Bojase, Gomotsang
Paddon-Row, Michael N.
Sherburn, Michael S.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (26) : 4836 - 4839
[17] PEARSON EL, UNPUB
[18] Merging and bifurcation of 4+2 and 2+4 cycloaddition modes in the archetypal dimerization of butadiene. A case of competing bispericyclic, pericyclic and diradical paths
Quadrelli, P
Romano, S
Toma, L
Caramella, P
[J]. TETRAHEDRON LETTERS, 2002, 43 (48) : 8785 - 8789
[19] The dimerisation of 2-methoxycarbonylbuta-1,3-diene: the importance of paralocalisation energy in assessing diene reactivity
Spino, C
Crawford, J
Cui, YP
Gugelchuk, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (06): : 1499 - 1506
[20] PREPARATION OF MIKANECIC ESTER AND ITS PRECURSOR, 1,3-BUTADIENE-2-CARBOXYLIC ESTER
SYDNES, LK
SKATTEBOL, L
CHAPLEO, CB
LEPPARD, DG
SVANHOLT, KL
DREIDING, AS
[J]. HELVETICA CHIMICA ACTA, 1975, 58 (07) : 2061 - 2073

← 1 2 →