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Search for "norbornadiene" in Full Text gives 26 result(s) in Beilstein Journal of Organic Chemistry.
Strategies in the synthesis of dibenzo[b,f]heteropines
Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51
- ] reported the synthesis of substituted dibenzo[b,f]azepines 110 as unexpected products during their investigation of the Catellani reaction. The Pd-catalysed reaction of an aryl iodide 106, bromoaniline 107, norbornadiene (108) and base resulted in the norbornene-azepine intermediate 109. Heating to 130 °C
Transition-metal-catalyzed domino reactions of strained bicyclic alkenes
Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38
- years [2][3][4][5][6]. Broadly speaking, bicyclic alkenes can be classified into two groups: homobicyclic and heterobicyclic alkenes. Homobicyclic alkenes are hydrocarbons, like norbornadiene, while heterobicyclic alkenes contain at least one heteroatom in the bicyclic framework. Typically, reactions
- in the case of heterobicyclic alkenes, the heteroatom. This preferential exo coordination is not always the case, as norbornadiene derivatives are known to preferentially form chelated endo complexes which can change the stereochemical outcome of the reaction. Nevertheless, the predisposition of
- noted decreasing the steric bulk of the amide moiety of the substrate from isopropyl to ethyl to methyl decreased the enantioselectivity of the reaction. Carbon- and nitrogen-bridging bicyclic alkenes were also identified as competent substrates. In this respect, norbornadiene was found to give the
Borylated norbornadiene derivatives: Synthesis and application in Pd-catalyzed Suzuki–Miyaura coupling reactions
Beilstein J. Org. Chem. 2022, 18, 368–373, doi:10.3762/bjoc.18.41
- Robin Schulte Heiko Ihmels Department of Chemistry and Biology, University of Siegen, and Center of Micro- and Nanochemistry and (Bio)Technology (Cμ); Adolf-Reichwein-Str. 2, 57068 Siegen, Germany 10.3762/bjoc.18.41 Abstract The photochromic norbornadiene/quadricyclane system is among the most
- -dioxaborolane was prepared and shown to be a suitable substrate for Pd-catalyzed Suzuki–Miyaura coupling reactions with selected haloarenes. It was demonstrated exemplarily that the novel monosubstituted 2-(1-naphthyl)norbornadiene, that is accessible through this route, is transformed to the corresponding
- quadricyclane upon irradiation, whereas the back reaction can be accomplished by thermal treatment. Keywords: molecular solar thermal system; Pd-mediated catalysis; photochemistry; photoswitches; quadricyclanes; Introduction Norbornadiene (1a, bicyclo[2.2.1]heptadiene) is a photochromic compound that has
Iridium-catalyzed hydroacylation reactions of C1-substituted oxabenzonorbornadienes with salicylaldehyde: an experimental and computational study
Beilstein J. Org. Chem. 2022, 18, 251–261, doi:10.3762/bjoc.18.30
- independently studied the rhodium-catalyzed intermolecular hydroacylation reaction of salicylaldehydes with norbornadiene derivatives. It was found that electron-donating moieties at the C1-position were well tolerated in the hydroacylation reaction giving methyl- (15b), ethyl- (15c), and t-Bu- (15d) adducts in
A study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolines
Beilstein J. Org. Chem. 2021, 17, 2051–2066, doi:10.3762/bjoc.17.132
- Abstract This work presents an examination of the selective functionalization of norbornadiene through nitrile oxide 1,3-dipolar cycloaddition/ring-opening metathesis (ROM)/cross-metathesis (CM) protocols. Functionalization of commercially available norbornadiene provided novel bicyclic scaffolds with
- of natural products (especially macrocycles) [12], alkaloids [13], amino acids and functionalized biomolecules such as peptides [14][15][16][17][18][19][20] or various drugs [21]. Due to the ring strain, bicyclic systems and derivatives, such as norbornadiene derivatives can easily be converted
- selective functionalization of readily available norbornadiene across nitrile oxide cycloaddition/ROM/CM protocols in view of the access of various fluorine-containing molecular entities as well as to explore the chemical behavior of olefin bonds in the reaction with some fluorinated alkene derivatives in
Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes
Beilstein J. Org. Chem. 2021, 17, 283–292, doi:10.3762/bjoc.17.27
- by 2018, the total number of publications and patents related to the production and use of norbornene and norbornadiene derivatives had exceeded 30,000 [58]. Indeed, norbornene and its derivatives have found application in medicine, agriculture, microelectronics, and rocket technology as well as in
- expected [80][81][82]. The treatment of norbornene 2l with t-BuOK resulted in the selective elimination of nitrous acid to form the desired monofluorinated norbornadiene 6 in 77% yield. No competitive elimination of HF was observed. The Diels–Alder reaction–base-induced HNO2 elimination sequence opens a
A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid
Beilstein J. Org. Chem. 2020, 16, 2534–2539, doi:10.3762/bjoc.16.205
- of diamond-like hydrocarbons, diamantane, in 65% yield by hydroisomerization of the norbornadiene dimer, endo-endo-heptacyclo[8.4.0.02,12.03,8.04,6.05,9.011,13]tetradecane (binor-S) on treatment with concentrated sulfuric acid (98%). In the presence of H2SO4 of lower concentration (75–80%), the
- compounds for the preparation of diamantane are three isomeric polycyclic hydrocarbons C14H20 3а–с, which are obtained by hydrogenation of the norbornadiene dimer, heptacyclo[8.4.0.02,12.03,8.04,6.05,9.011,13]tetradecane (binor-S, 2). Binor-S is hydrogenated in the presence of a platinum catalyst (Н2PtCl6
NMR Spectroscopy of supramolecular chemistry on protein surfaces
Beilstein J. Org. Chem. 2020, 16, 2505–2522, doi:10.3762/bjoc.16.203
- groups of Lys and Arg, often combined with a moiety that cradles the hydrophobic portion of the aliphatic side chain. Supramolecular tweezers consist of alternating benzene and norbornadiene units and thread the side chain of Lys or Arg into their aromatic cavity. In addition, an ion pair interaction is
Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners
Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186
- accessible compound, namely norbornadiene (10) by involving oxidative aromatization in the presence of DDQ via an intermediate 17, as displayed in Scheme 2. As can be seen from an inspection of Scheme 2, they first performed a single step cyclotrimerization of 10 using n-BuLi and t-BuOK in 1,2-dibromoethane
- /mol) transformation of 12 (syn) to 17, calculated by density functional theory (DFT) calculations. On the other hand, in 2008, Higashibayashi et al. reported the synthesis of first chiral C3-symmetric trimethylsumanene 28 starting from enantiopure norbornadiene (10) by employing a rational synthetic
Reactions of 3-aryl-1-(trifluoromethyl)prop-2-yn-1-iminium salts with 1,3-dienes and styrenes
Beilstein J. Org. Chem. 2020, 16, 2064–2072, doi:10.3762/bjoc.16.173
- sequence. On the other hand, the successful thermal iminium-ion induced SE(Ar) reactions shown in Scheme 2 were not applicable to the iminium-substituted norbornadiene 2, which suffered undefined polymerization on moderate heating in various solvents. In contrast to so far unknown 9‑amino-9
Pauson–Khand reaction of fluorinated compounds
Beilstein J. Org. Chem. 2020, 16, 1662–1682, doi:10.3762/bjoc.16.138
- transformation widely used in the synthesis of polycyclic complex molecules. The intermolecular variant shows a wide alkyne scope, but in terms of the olefin counterpart is limited to the use of ethylene or strained alkenes, such as norbornene and norbornadiene. The high prevalence of five-membered ring systems
- Co–C bond. These electronic effects have been shown to be less important than steric ones, and are often overcome by the latter. Regarding the stereochemistry, exo-products are almost exclusively obtained for norbornene and norbornadiene. Many deviations from the classic reaction conditions have been
- selectivity of simple alkenes. In this regard, most examples have been restricted to the use of ethylene or strained alkenes such as cyclopropene, norbornene, norbornadiene, (E)-cyclooctene, or bicyclo[3.2.0]hept-6-ene [67][68][69]. The first example of an intermolecular version of fluorinated compounds was
Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas
Beilstein J. Org. Chem. 2020, 16, 645–656, doi:10.3762/bjoc.16.61
- )2, Rh(acac)(CO)2, [RhCl(COD)]2, Rh(MeCN)2(COD)BF4, Rh(COD)BF4, Rh(COD)2OTf, [Rh(OMe)(COD)]2, Rh(OAc)2, [Rh(CF3COO)]2, [Rh(CH3(CH2)6CO2)2]2, Rh(acac)3, Rh(ethylene)2(acac), [Rh(ethylene)2Cl]2, Rh(norbornadiene)2BF4, [Cp*RhCl2]2, Rh/C, and RhCl3·3H2O), ligands containing nitrogen or phosphorus (PP3
Norbornadiene-functionalized triazatriangulenium and trioxatriangulenium platforms
Beilstein J. Org. Chem. 2019, 15, 1815–1821, doi:10.3762/bjoc.15.175
- (NBD) and quadricyclanes (QC) attached to TATA and TOTA platforms which can be used to check if these accelerated rates and the spin change mechanism also apply to [2 + 2] cycloreversions (QC→NBD). Keywords: [2 + 2] cycloaddition; [2 + 2] cycloreversion; norbornadiene; photochemical isomerization
- the mechanisms of bulk metal catalysis and open new ways to design new catalytic systems. Towards this end, and following the “platform concept”, we designed a cyano-substituted norbornadiene, which is functionalized with an acetylene spacer on a TATA platform to investigate an eventual “spin
- -catalysed” [2 + 2] cycloreversion on bulk gold of quadricyclane 1b to norbornadiene 1a (Figure 1). The cycloreversion of most quadricyclane systems proceeds smoothly in solution upon irradiation in the presence of triplet sensitizers [7]. If 1b is adsorbed on a gold surface the bulk gold could take the role
A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction
Beilstein J. Org. Chem. 2019, 15, 291–298, doi:10.3762/bjoc.15.26
- palladium-catalyzed reaction that results in phenanthrene derivatives using aryl iodides, ortho-bromobenzoyl chlorides and norbornadiene in one pot. This dramatic transformation undergoes ortho-C–H activation, decarbonylation and subsequent a retro-Diels–Alder process. Pleasantly, this protocol has a wider
- substrate range, shorter reaction times and higher yields of products than previously reported methods. Keywords: C–H activation; norbornadiene; palladium; phenanthrene derivatives; Introduction Phenanthrene is a polycyclic aromatic hydrocarbon which contains three benzene rings. The phenanthrenes can be
- scope and relatively low reaction efficiency. Very recently, Fuk Yee Kwong and co-workers (Scheme 1d) developed a straightforward one pot π-extension method using norbornadiene instead of norbornene as directing group to afford the phenanthrenes [11]. However, ortho-haloaryl carboxylic acids employed in
Olefin metathesis in multiblock copolymer synthesis
Beilstein J. Org. Chem. 2019, 15, 218–235, doi:10.3762/bjoc.15.21
- norbornadiene (NB–(PPE–PMI)–NB) to allow further functionalization through olefin metathesis. The separately prepared by ROMP living diblock copolymers comprising norbornene with OEG (A block) and an NHS (B block) were synthesized in the presence of Gr1 and terminated by the reaction with NB–(PPE–PMI)–NB to
A tutorial review of stereoretentive olefin metathesis based on ruthenium dithiolate catalysts
Beilstein J. Org. Chem. 2018, 14, 2999–3010, doi:10.3762/bjoc.14.279
- norbornadiene was also investigated by Hoveyda [16]. A highly syndiotactic polymer was obtained by fine tuning of the steric and electronic characteristics of the catalyst (not depicted in this review) [16]. ROCM reactions of norbornene (1) with styrene (5) could be carried out with only one mole percent of
Ring-opening metathesis of some strained bicyclic systems; stereocontrolled access to diolefinated saturated heterocycles with multiple stereogenic centers
Beilstein J. Org. Chem. 2018, 14, 2698–2707, doi:10.3762/bjoc.14.247
- Recently, we have demonstrated the high utility of various constrained cyclic dienes, such as norbornadiene as well as 1,5- and 1,3-cyclooctadienes in the context of their applicability towards the access of diverse, highly functionalized olefinated molecules [14][15][16]. The corresponding β-lactams
Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source
Beilstein J. Org. Chem. 2018, 14, 2435–2460, doi:10.3762/bjoc.14.221
- α,β-unsaturated carboxylic acids 28 using [RhCl(nbd)]2 (nbd = norbornadiene) as a catalytic precursor (Scheme 25) [54]. When an alkyl-substituted substrate was examined, the p-methoxy-substituted dppp derivative was found to be the suitable ligand. For this transformation, the reaction mechanism
Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides
Beilstein J. Org. Chem. 2018, 14, 772–785, doi:10.3762/bjoc.14.65
- with pentanone 37 results in carbocyclic C-nucleosides with a C1'-hydroxy group (38 and 39, respectively, Figure 12A) [52][53]. They synthesized cyclopentanone 37 in 7 steps starting from norbornadiene (40, Figure 12B). Furthermore, silyl protection (TIPS) of the C2' and C3' was observed to be critical
- substitution on cyclopentanone gives C1'–OH carbocyclic C-nucleosides. B. Synthesis of cyclopentanone from norbornadiene and substituents that facilitate carbocyclic C-nucleoside syntheses. Synthesis of carbocyclic C-nucleosides via Suzuki coupling [53]. A. Synthesis of OTf-cyclopentene that enable Suzuki
Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines
Beilstein J. Org. Chem. 2015, 11, 2097–2104, doi:10.3762/bjoc.11.226
- 10–14, the addition of 1.2 equiv of cyclooctadiene (COD), cyclooctene (COE), norbornadiene (NBD), 1-octene, and dibenzylideneacetone (dba) all improved the yield of the Chan–Lam reaction, but COD was most efficient. Having identified optimal conditions for the synthesis of N-cyclohexenylnitrone 8aa
Grubbs–Hoveyda type catalysts bearing a dicationic N-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids
Beilstein J. Org. Chem. 2015, 11, 1632–1638, doi:10.3762/bjoc.11.178
- as the organic solvent. While Ru-2 showed low RCM activity, it turned out to be active in ROMP reactions of strained cyclic olefins like norbornenes, 7-oxanorbornenes, norbornadiene and cis-cyclooctene allowing for the synthesis of the corresponding polymers with unprecedented low metal contamination
Superoxide chemistry revisited: synthesis of tetrachloro-substituted methylenenortricyclenes
Beilstein J. Org. Chem. 2014, 10, 2531–2538, doi:10.3762/bjoc.10.264
- nortricyclenes using palladium and zinc powder from norbornadiene. The bromination of norbornene [30][31][32] is another route to the nortricyclenes. Here, in this study we report an efficient method for the synthesis of aryl- and vinyl-substituted tetrachloromethylenenortricyclenes from the Diels–Alder (DA
Thermochemistry and photochemistry of spiroketals derived from indan-2-one: Stepwise processes versus coarctate fragmentations
Beilstein J. Org. Chem. 2013, 9, 1668–1676, doi:10.3762/bjoc.9.191
- chelotropic elimination of 1,3-dioxolan-2-ylidene is not likely. This carbene has been generated from a norbornadiene spiro ketal, and it cleanly fragmented into CO2 and ethylene [30]. Theoretical calculations support the low barrier for fragmentation [31]. We explain the different reaction behaviour of our
- spiroketal 1 by the fact that two energetically unfavourable products would have to be formed (a quinodimethane and a carbene), whereas the fragmentation of the norbornadiene ketal gives benzene and a carbene. The mechanism for the thermal decomposition of 2 is likely to be similar. The high yield of
Towards a biocompatible artificial lung: Covalent functionalization of poly(4-methylpent-1-ene) (TPX) with cRGD pentapeptide
Beilstein J. Org. Chem. 2013, 9, 270–277, doi:10.3762/bjoc.9.33
- -norbornadiene 6, by using classical coupling chemistry, which resulted in polymers 7a and 7b, respectively (Scheme 1). The alkyne-containing amino acid 5 was prepared according to Brea et al. [15] Membrane 7a, synthesized from polymer 4 and amino acid 5, was coupled with RGD peptide 1b, bearing an azido group
Synthesis and Diels–Alder cycloaddition reaction of norbornadiene and benzonorbornadiene dimers
Beilstein J. Org. Chem. 2009, 5, No. 39, doi:10.3762/bjoc.5.39
- Bilal Nisanci Erdin Dalkilic Murat Guney Arif Dastan Atatürk University, Faculty of Science, Department of Chemistry, 25240 Erzurum-TURKEY 10.3762/bjoc.5.39 Abstract Dimeric forms of norbornadiene and benzonorbornadiene were synthesized starting with known monobromide derivatives. The Diels–Alder
- cycloaddition reaction of dimers with TCNE and PTAD was investigated and new norbornenoid polycyclics were obtained. All compounds were characterized properly using NMR spectroscopy. Keywords: benzonorbornadiene; Diels–Alder reaction; norbornadiene; Stille coupling; Introduction Norbornadiene (1) and related
- rearrangement [12][13][14][15], as well as in other instances [16][17][18][19][20][21][22]. Therefore, functionalizations of these compounds are important. In this study, we investigated the synthesis and Diels–Alder cycloaddition reaction of norbornadiene and benzonorbornadiene dimers. Results and Discussion
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