Carbon-carbon double bond isomerization in heterocyclic hydrazine derivatives

被引：1

作者：

Ilisson, Mihkel ^{[1
]}

Tomson, Kristjan ^{[1
]}

Tamm, Tarmo ^{[2
]}

Maeorg, Uno ^{[1
]}

机构：

[1] Univ Tartu, Inst Chem, 14a Ravila, EE-50411 Tartu, Estonia

[2] Univ Tartu, Inst Technol, 1 Nooruse, EE-50411 Tartu, Estonia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2018年 / 54卷 / 05期

关键词：

enamides; hydrazine derivatives; heterocyclic chemistry; homogeneous catalysis; isomerization; RING-CLOSING METATHESIS; RUTHENIUM HYDRIDE; ENAMIDES; MOIETY;

D O I：

10.1007/s10593-018-2308-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Double bond isomerization by in situ generated ruthenium hydride catalyst in 6- to 9-membered hydrazine heterocycles including an endocyclic N-N bond was investigated. Based on the results of the experiments, a conclusion was made that the generation of resonance-stabilized enehydrazides is generally favored, but in some cases, the reaction pathway is presumably also highly dependent of steric interactions. With the current method, two novel enehydrazide heterocycles and one enehydrazine heterocycle were produced and characterized.

引用

页码：572 / 575

页数：4

共 50 条

[41] Rotational energy barrier of the polarized carbon-carbon double bond in quinophthalone
Yavari, I
Adib, M
Bijanzadeh, HR
Sadegi, MMM
Logmani-Khouzani, H
Safari, J
MONATSHEFTE FUR CHEMIE, 2002, 133 (08): : 1109 - 1113
[42] ADDITION OF CARBENE ANTHRONYLIDENE ON DOUBLE BOND CARBON-CARBON - STERIC EFFECTS IN CASE OF ETHYLENE AND ITS PHENYL DERIVATIVES
CAUQUIS, G
REVERDY, G
TETRAHEDRON LETTERS, 1968, (09) : 1085 - &
[43] CARBON-CARBON DOUBLE-BOND FORMING REACTIONS OF COORDINATED CARBON-MONOXIDE
MOLOY, KG
MARKS, TJ
ACS SYMPOSIUM SERIES, 1983, 211 : 544 - 544
[44] Formation of Carbon-Carbon Double Bond between Cp Ligand and Alkenyl Carbon of Titanacyclopentenes
Takahashi, Tamotsu
Nakata, Hiroki
Bando, Masayoshi
Song, Zhiyi
SYNLETT, 2024,
[45] HYDROBORATION OF EXTRACYCLIC CARBON-CARBON DOUBLE BONDS CONJUGATED WITH AN INTRACYCLIC CARBON-NITROGEN DOUBLE BOND OR WITH A HETEROCYCLIC CHAIN OF C=C-C=N TYPE
ARNAUD, JM
RUMPF, P
VIEL, C
COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1969, 268 (01): : 107 - &
[46] Rh-based Biphasic Isomerization of Carbon-Carbon Double Bonds in Natural Oils
Quirino, Rafael L.
Larock, Richard C.
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 2012, 89 (06) : 1113 - 1124
[47] Ultrafast carbon-carbon single-bond rotational isomerization in room-temperature solution
Zheng, Junrong
Kwak, Kyungwon
Xie, Jia
Fayer, M. D.
SCIENCE, 2006, 313 (5795) : 1951 - 1955
[48] Cleavage of the carbon-carbon bond in α-glycols under the action of bismuth(v) derivatives
N. V. Dolganova
V. A. Dodonov
T. I. Zinov'eva
I. G. Prezhbog
Russian Chemical Bulletin, 1997, 46 : 1164 - 1166
[49] THE CLEAVAGE OF CARBON-CARBON BOND IN THE DERIVATIVES OF BARENECARBOXYLIC ACIDS UNDER THE ACTION OF BASES
ZAKHARKIN, LI
CHAPOVSKY, YA
TETRAHEDRON LETTERS, 1964, (19-2) : 1147 - 1150
[50] Chemical and electrochemical oxidative activation of arenol derivatives for carbon-carbon bond formation
Quideau, S
Pouységu, L
Deffieux, D
CURRENT ORGANIC CHEMISTRY, 2004, 8 (02) : 113 - 148

← 1 2 3 4 5 →