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1.
1,3-Di-tert-butylazulene reacted with highly electrophilic trifluoromethanesulfonate of N-containing heterocycles to give 5-(dihydroheteroaryl)azulene derivatives in good yield and treatment of the 5-(dihydroheteroaryl)azulene derivatives with KOH afforded 5-(heteroaryl)azulenes in excellent yield. 相似文献
2.
A series of four new azulene-1,5-diol diastereomers were prepared and found to exhibit large differences (ΔRf 0.22–0.46) in silica TLC mobilities despite having stereocenters four bonds apart. The stereoisomers were identified by X-ray crystallography, and in all cases the RR/SS diastereomers were less strongly retained than the RS/SR diastereomers. The crystal structures suggested that this is due to a conformational preference for the CF3 groups to be nearly perpendicular to the plane of the azulene ring, which caused the dihedral angle between the OH groups to be larger (in the RR/SS diastereomers) or smaller (in the RS/SR diastereomers). The smaller dihedral angles allow the RS/SR diastereomers to simultaneously bind to a silica surface and thus be more strongly retained. Two similar benzene derivatives and several cycloalkanediols with more proximate stereocenters showed little or no difference in mobilities between diastereomers, though the NMR differences were greater. Thus, the azulene ring is an important factor in enforcing the conformational preferences, either through steric interactions with the 4/8 substituents (H or methyl) or its significant dipole moment, or both. 相似文献
3.
Paul Cowper Yu Jin Michael D. Turton Gabriele Kociok‐Khn Simon E. Lewis 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2016,128(7):2610-2614
Azulenesulfonium salts may be readily prepared from the corresponding azulenes by an SEAr reaction. These azulene sulfonium salts are bench‐stable species that may be employed as pseudohalides for cross‐coupling. Specifically, their application in Suzuki–Miyaura reactions has been demonstrated with a diverse selection of coupling partners. These azulenesulfonium salts possess significant advantages in comparison with the corresponding azulenyl halides, which are known to be unstable and difficult to prepare in pure form. 相似文献
4.
This review shows the unusual physicochemical properties and wide application of azulene and its derivatives. The recent synthesis strategies of kinds of substituted azulene are also listed. 相似文献
5.
Ai Ito Takamasa Amaki Ayako Ishii Kazuo Fukuda Ryu Yamasaki Iwao Okamoto 《Tetrahedron letters》2018,59(45):3994-3998
Aromatic amides bearing 2-azulenyl group on the amide nitrogen were synthesized and their structures were investigated. The π-electron density of the N-aryl group was found to influence the cis-trans conformational preferences of these compounds in solution. X-ray crystallography revealed that the plane of the 2-azulenyl ring has a strong tendency to lie coplanar with the amide plane when the azulene group is located on the same side as the amide oxygen atom. 相似文献
6.
Stefan Schmitt Martin Baumgarten Joachim Simon Klaus Hafner 《Angewandte Chemie (International ed. in English)》1998,37(8):1077-1081
Simply mixing solutions of the title compound 1 and tetrathiafulvene (TTF) in acetonitrile provides the charge-transfer complex 2 . Here, 1 functions as a novel electron acceptor and is present in the complex as a radical anion. An electrical conductivity of up to 3 S cm−1 was determined for 2 with a two-point powder measurement. 相似文献
7.
In the presence of an active Ir-based catalyst, azulene underwent stepwise borylation with bis(pinacolato)diboron to produce polyborylated products. The reactivity of the ring atoms toward borylation was found to decrease in the following order: 2-position>1,3-positions>6-position>5,7-positions. Extension of the borylation to some azulenes substituted at the five-membered ring was also examined. Furthermore, the reaction of 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)azulene (3a) with an equivalent of hydrogen peroxide revealed that the oxidation proceeds preferentially at the 6-position. This indicates that the reactivity of the boryl group is governed by the π-polarization of the azulenyl skeleton. 相似文献
8.
Ysaura De Sanctis Alejandro J. Arce Ruben Machado Teresa González 《Journal of organometallic chemistry》2004,689(11):2025-2028
The cluster [Os3(CO)10(MeCN)2] reacts readily with azulene in refluxing cyclohexane to give the oxidative addition product [Os3(μ-H)(μ2-η1-C10H7)(CO)10] 1 which was shown by its X-ray crystal structure to contain the C5 ring of the azulenyl ligand bonded through a single carbon atom at the 1-position. We propose that the compound is zwitterionic, with the 7-membered ring a tropylium cation and the 5-membered ring coordinated as a μ-alkylidene to the metal cluster, which carries a formal negative charge. Thermal loss of one CO ligand leads by further oxidative addition to the known cluster [Os3(μ-H)2(μ3-η1:η1:η1-C10H6)(CO)9] 2. 相似文献
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10.
The current study has obtained excellent potential nonlinear optical(NLO) materials by combining density functional theory methods with sum-over-states model to predict the second order NLO properties of helical graphene nanoribbons(HGNs) through introducing azulene defects or/and BN units. The introduction of these functional groups deforms the pristine HGN (compression or tension) and enhances obviously the static first hyperpolarizability(<b0>) of system by up to two orders of magnitude. The tensor components along the helical axis of HGNs play a dominant role in the total <b0>. The azulene defects and the BN units polarize the pristine HGN to different degrees, and the azulenes and contiguous benzenes are involved in the major electron excitations with significant contributions to <b0> but the BN units are not. The BN-doped chiral HGNs have good kinetic stability and strong second order NLO properties(6.84×105×10-30 esu), and can be a potential candidate of high-performance second order NLO materials. The predicted two-dimensional second order NLO spectra provide useful information for further exploration of those helicenes for electro-optic applications. 相似文献