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Search for "phospholes" in Full Text gives 9 result(s) in Beilstein Journal of Organic Chemistry.
Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles
Beilstein J. Org. Chem. 2021, 17, 671–677, doi:10.3762/bjoc.17.56
- and derivatization of trivalent phosphole F and the optical properties have not been clarified. The systematic knowledge of the properties of a new family of fused phospholes is valuable for the design of new types of functional π-electron-containing materials. This paper presents the synthesis
- . The reaction of 2 with borane in THF formed a borane complex 6 in 91% yield, and the reaction with chloro(dimethyl sulfide)gold afforded the gold complex 7 in 39% yield. The molecular structures of the synthesized phospholes 2−7 were confirmed by spectral analyses (1H, 13C, and 31P NMR as well as MS
- and IR). All the corresponding aromatic proton and carbon atoms on the two naphthalene rings were equivalent in the 1H and 13C NMR spectra of phospholes. These results show that all phosphole derivatives had a symmetric structure in solution. The 31P NMR spectra of these show the typical low-field
Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides
Beilstein J. Org. Chem. 2020, 16, 818–832, doi:10.3762/bjoc.16.75
- importance for biologically active compounds, as specific functional groups are necessary to have a desired biological activity. Considering the functionalization of the five-membered P-heterocycles, the derivatives containing double bond(s) (i.e., phospholenes or phospholes) are of special importance, as a
Synthesis of triphenylene-fused phosphole oxides via C–H functionalizations
Beilstein J. Org. Chem. 2020, 16, 524–529, doi:10.3762/bjoc.16.48
- -emitting diodes [14]. Recently, Saito et al. reported the synthesis of phosphorus-bridged triphenylenes, that is, triphosphasumanene trisulfides, and demonstrated their capability as a junction for single-molecule conductors [15]. The synthesis of PAH-fused phospholes typically requires efficient methods
- synthesis of π-extended phospholes. In this respect, our attention focused on the fusion of phosphole with triphenylene, which represents one of the most common disc-like PAH motifs in organic materials chemistry [19][20][21][22][23][24][25]. Herein, we report on the synthesis of triphenylene-fused
- , entry 3). Like many 2,3-dialkylbenzo[b]phospholes [17][35], 8a–c showed strong fluorescence in solution (ΦF = 0.67 and 0.34 for 8a and 8b, respectively). In contrast to the highly resolved bands in the absorption spectra, the fluorescence spectra were rather simple, with distinct emission peaks at 452
Atom-economical group-transfer reactions with hypervalent iodine compounds
Beilstein J. Org. Chem. 2018, 14, 1263–1280, doi:10.3762/bjoc.14.108
- group can be successfully employed in further derivatisations. In example, indenones 40 and phospholes 41 could smoothly be generated. In contrary to this unexpected reaction pathway, Waser and co-workers particularly aimed for an atom-economical application of EBX reagents 36a utilizing a copper
Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives
Beilstein J. Org. Chem. 2017, 13, 2304–2309, doi:10.3762/bjoc.13.226
- ; photophysical property; Introduction The chemistry of phospholes, fully unsaturated five-membered heterocyclic rings containing a phosphorus element, has drawn much attention in terms of the development of synthetic methods and elucidation of its spectroscopic properties for applications in organic field
- substituent has been reported for several phosphine sulfide (P=S) compounds [10][15][17][20]. The cationic phospholium 7 exhibited green fluorescence (λem = 465 nm) with the largest red shift of this series of phospholes owing to the cationic nature of the phosphorus atom, providing particularly strong
- center. Because of the cationic nature of the phosphorus center, the energy levels in cationic phospholium 7 are significantly stabilized. In contrast to the fluorescent phospholes, calculations show that the HOMO and HOMO−1 of nonfluorescent phosphole sulfide 5 and selenide 6 have a large contribution
Aluminacyclopentanes in the synthesis of 3-substituted phospholanes and α,ω-bisphospholanes
Beilstein J. Org. Chem. 2016, 12, 406–412, doi:10.3762/bjoc.12.43
- substituted phospholenes [6] and phospholes [7] has been reported. This approach was used to obtain materials for light-emitting diodes (LEDs) [8], phosphorus-containing polymers [9][10], bisphospholes [11], bicyclodiphospholanes and spirobicyclodiphospholanes [12][13]. However, this method is faced with some
- , in our opinion, the development of these reactions would give rise to practically promising one-pot methods for the preparation of a broad range of cyclic and acyclic organophosphorus compounds of specified structure (phospholanes, phospholenes, phospholes and 1,2- and 1,4-diphosphorus compounds
Enhancing the reactivity of 1,2-diphospholes in cycloaddition reactions
Beilstein J. Org. Chem. 2015, 11, 169–173, doi:10.3762/bjoc.11.17
- : cycloaddition; phospholes; phosphorus heterocycles; polycyclic phosphines; retro-Diels–Alder reaction; Introduction Phospholes are weakly aromatic heterocycles and demonstrate rather different properties from those of their S, N and O counterparts [1][2]. Due to low their aromaticity, phospholes are of
- significant interest for the preparation of highly effective catalysts, materials for light-emitting diodes and nonlinear optics [3][4]. In contrast to furans, thiophenes and pyrroles, phospholes display cycloaddition and complexation reactions and can be used as starting materials for caged phosphines
- theoretical calculations and experimental work [7][8]. At the same time both the presence of the P=C bond in phospholes as well as the transient 2H-phospholes [3] increase the cycloaddition reactivity. It was previously demonstrated that 1-alkyl-1,2-diphospholes combine the properties of both 1H-phospholes
Phosphinate-containing heterocycles: A mini-review
Beilstein J. Org. Chem. 2014, 10, 732–740, doi:10.3762/bjoc.10.67
- . Selected recent synthetic work by us and others is presented below. Review Phospholes Several compounds have been prepared in this series. Keglevich and coworkers realized the synthesis of phosphole derivatives 2a–f based on the McCormack reaction [10] followed by microwave-assisted esterification of the
- phosphinic acid using different alcohols in large excess (Scheme 1) [11][12]. Six phospholes 2a–f were prepared in yields up to 94%. Montchamp and coworkers have synthesized phospholes 4a,b by ring closing metathesis using 2 or 5 mol % of 2nd generation Grubbs’ catalyst (Scheme 2) [13][14]. Two compounds 4a
Asymmetric Diels–Alder reaction with >C=P– functionality of the 2-phosphaindolizine-η1-P-aluminium(O-menthoxy) dichloride complex: experimental and theoretical results
Beilstein J. Org. Chem. 2013, 9, 392–400, doi:10.3762/bjoc.9.40
- azaphosphole was reported by Arbuzov and co-workers [10]. Subsequently, pioneering work by the research group of Appel established several interesting features associated with the DA reactions of phosphaalkenes [11][12]. Mathey and co-workers showed that 1H-phospholes underwent a 1,5-H shift followed by
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