… of p -TsOH at 180 °C for 4 hours (Scheme 2). The presence of trimethylamine during the pyrolysis significantly increases the yield of sym-carborane-2,4. Europe PMC. Please check your email for instructions on resetting your password. The full text of this article hosted at iucr.org is unavailable due to technical difficulties. 181–189. "New ligand platforms featuring boron-rich clusters as organomimetic substituents", "H+, CH3+, and R3Si+Carborane Reagents: When Triflates Fail", "New keys for old locks: carborane-containing drugs as platforms for mechanism-based therapies", https://en.wikipedia.org/w/index.php?title=Carborane&oldid=1015995471, All Wikipedia articles needing clarification, Wikipedia articles needing clarification from December 2020, Creative Commons Attribution-ShareAlike License, This page was last edited on 4 April 2021, at 20:13. Synthesis and evaluation of transthyretin amyloidosis inhibitors containing carborane pharmacophores. The process is general and provides an important new synthetic strategy for the preparation of functionalized boron clusters. Synthesis Attempts And Plausible Applications Of Dithiolated Ortho –Carboranyl Transition Metal Complexes And Synthesis Of Bulky Terphenyls Surendra Bahadur Karki University of South Carolina Follow this and additional works at:https://scholarcommons.sc.edu/etd Part of theChemistry Commons This Open Access Thesis is brought to you by Scholar Commons. YAMAMOTO, Y.; SEKO, T.; NAKAMURA, H.; NEMOTO, H. 1993-10-26 00:00:00 ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. [21][22] C-functionalized carboranes represent a source of boron for boron neutron capture therapy. Soc. However, the versatility in this chemistry can be further extended via introduction of functional groups at boron locations, as will be described … Carboranes and boranes adopt 3-dimensional cage (cluster) geometries in order to facilitate their electron-delocalized nonclassical bonding, whereas hydrocarbons are typically chains or rings; for example, B4H10 has an arachno cage geometry, while the butane isomers n- and iso-C4H10, with 4 more electrons than B4H10, adopt linear or branched chain structures. Am. Many dicarbaboranes exist as isomers that differ in the relative location of the carbon centers. The carboranes containing uridine derivatives (9a,b,c), and purine base (8) were prepared by the reaction of decaborane with the corresponding acetylene precursors (3a, 3b, 2c and 5b, respectively). Synthesis and Structure of m-Carborane 7-3. We have aimed to understand their electronic property, reactivity and to apply their spherical geometry for design and synthesis … Beer, D. C.; Miller, V. R.; Sneddon, L. G.; Grimes, R. N.; Mathew, M.; Palenik, G. J. J. [1], [4], and [5][clarify]). Synthesis of 3-amino-1-carboxy-o-carborane and an improved, general method for the synthesis of all three C-amino-C-carboxycarboranes 1.8 Synthesis of Ortho-Carboranes 13 1.9 Reactivity of Ortho-Carboranes 15 1.10 Nido-Carboranes 16 1.11 The Dicarbollide Dianion 18 1.12 Metallocarboranes 19 1.13 The Medicinal Chemistry of Carboranes 20 1.14 Re and 99 mTcf 9 Tc-Metallocarboranes and Radiopharmaceuticals 21 1.15 Carboranes as Pharmacophores 24 1.16 Scope and Summary … 1995, 117, 12227. 1973, 95, 3046. These features of carboranes may allow wide variety of application for molecular construction, medicinal chemistry and materials sciences. The icosahedral CB11H12− anion has a strong conjugate acid, whose polychlorinated derivative H(CHB11Cl11) is even a superacid. Am. We describe in this article the synthesis and structural characterization of 15- and 16-vertex closo-carboranes as well as 16-vertex ruthenacarborane. If you do not receive an email within 10 minutes, your email address may not be registered, However, little attention has been paid to the understanding their nature in view of synthetic organic chemistry. The use of polyhedral carboranes for creation of these products is a discernable trend . Mercury Derivatives 7. [8][9] One-carbon reagents include cyanide, isocyanides, and formaldehyde. [1] Like many of the related boron hydrides, these clusters are polyhedra or fragments of polyhedra, and are similarly classified as closo-, nido-, arachno-, hypho-, etc., based on whether they represent a complete (closo-) polyhedron or a polyhedron that is missing one (nido-), two (arachno-), three (hypho-), or more vertices. Chem. Monocarboranes are clusters with BnC cages. [14] The bulk of the work on metallacarboranes has centered on 12-vertex MC2B9 and M2C2B8 clusters and 7-vertex MC2B4 and M2C2B3 (triple-decker[15] and multidecker sandwich[16]) clusters, but metallacarboranes of 6 to 15 vertices have also been prepared,[17][18] as have clusters with varying numbers of carbon, boron, and metal atoms (see refs. Learn about our remote access options, Department of Chemistry, Faculty of Science, Tohoku University, Sendai 980, Japan. It … Julius RL(1), Farha OK, Chiang J, Perry LJ, Hawthorne MF. Sigma-Bonded Transition Metal Derivatives 6-15. Fig. Abstract : Carborane-2,5 is the major volatile carborane formed from the pyrolysis of dihydrocarboranes 2,4. • Carboranes are member of a class of organometallic compounds containing carbon (C), boron (B), and hydrogen (H). For example, the high-temperature reaction of pentaborane(9) with acetylene affords several closo-carboranes as well as other products: Synthesis, characterisation, and biodistribution of radioiodinated C-hydroxy-carboranes. The carboranes containing uridine derivatives (9a,b,c), and purine base (8) were prepared by the reaction of decaborane with the corresponding acetylene precursors (3a, 3b, 2c … The carborane-fused thiophene (8) was synthesized as colorless crystals in 80% yield via solvent-free dehydration in the presence of 1 equiv. Designed synthesis of carboranes and metal—carborane complexes 849 As shown, the principal pathways that have been established or are under study utilize nido-RR'C2B4H6 derivatives whose R groups are attached to cage carbon atoms. Carboranes are a notable example of heteroboranes. Polyhedral carboxymethyl carborane (C 2 B 10 H 12) derivatives, including mono‐ and disubstituted o ‐, m ‐, and p ‐isomers, have been synthesized. Menu. Supramolecular host–guest complexation of these derivatives with cyclodextrins (CDs; namely, α‐, β‐, and γ‐CD) has been investigated in water. Use the link below to share a full-text version of this article with your friends and colleagues. [2] These boron-rich clusters exhibit unique organomimetic properties with chemical reactivity matching classical organic molecules, yet are structurally similar to metal-based inorganic and organometallic species[3], The C2B10H12 isomers, together with other carborane clusters and metallacarboranes (see below) are utilized in a wide range of applications, including heat-resistant polymers, recovery of radioactive metals from nuclear waste, catalysis, novel electroactive materials, and medical applications. [23], Some metal complexes exhibit catalytic properties. and you may need to create a new Wiley Online Library account. Electron-delocalized bonding in boranes and carboranes is discussed extensively in, The Wade–Mingos rules were first stated by. [26], Tricarba, tetracarba, pentacarba, and hexacarba clusters, For general overviews of carborane chemistry, see "Chemistry of the Elements", pp. However, many attempts to the synthesis of carboranes with more than 14 vertices had been unsuccessful since the report of a 14-vertex carborane in 2005. suggested [78] an approach based on the production of bis -trichlorosilyl derivative of o -carborane, which undergoes hydrolysis followed by … Chem. In addition to the closo-C2BnHn+2 series mentioned above, several open-cage dicarbon species are known including nido-C2B3H7 (isostructural and isoelectronic with B5H9) and arachno-C2B7H13. In addition to the three previously mentioned icosahedral C2B10H12 compounds, isomerism is also found in some smaller closo-carborane systems, e.g., 1,2- and 1,6-C2B4H6, 2,3- and 2,4-C2B5H7, 1,2- and 1,6-C2B6H8, and 2,3- and 2,4-C2B5H7, as well as in open-cage carboranes such as 2,3- and 2,4-C2B4H8 and 1,2 and 1,3-C2B9H13. Bach, B.; Nie, Y.; Pritzkow, H.; Siebert, W. J. Organomet. [25] It protonates fullerene, C60. Carboranes have been prepared by many different routes, the most common being addition of alkynyl reagents to boron hydride clusters to form dicarbon carboranes. Carboranes have as few as 5 and as many as 14 atoms in the cage framework (15 if metal atoms are included) are known, but the majority have two cage carbon atoms; of these, the best-known series is that of the closo-C2BnHn+2 systems, where n = 3 to 12. We report herein an efficient method to achieve chiral-at-cage arylation of o-carboranes with high regio- and enantioselectivities by a strategy of palladium-catalyzed asymmetric intramolecular … Synthesis of B(4)-Alkynylated o-Carboranes. Syntheses, properties, and synthetic applications of 13-vertex closo- and nido-carboranes are reported. Soc. To access a ChemInform Abstract of an article which was … Working off-campus? Scheme 2 Synthesis of carborane-fused thiophene (8). These compounds vary widely in composition, size (5 to 13 vertexes), cage geometry, method of synthesis, and properties, but some correlations are noted. [12], These dilithiated compounds react with a variety of electrophiles, e.g. Synthesis of Schiff Bases Derived from the Ammoniaundecahydro-closo-dodecaborate(1−) Anion, [B12H11NHCHR]-, and Their Reduction into Monosubstituted Amines [B12H11NH2CH2R]-: A New Route to Water Soluble Agents for BNCT. • General formula of carboranes is C2BnHn+m, where … Ortho-carborane is the organoboron compound with the formula C 2 B 10 H 12.The prefix ortho is derived from ortho.It is the most prominent carborane.This derivative has been considered for a wide range of applications from heat-resistant polymers to medical applications. One more method for production of carborane-containing silsesquioxanes is the sol-gel technique. Syntheses of icosahedral closo-dicarbadodecaborane derivatives (R2C2B10H10) employ alkynes as the R2C2 source and decaborane (B10H14) to supply the B10 unit. Synthesis of new polymeric materials ² films , coatings , elastomers , fibers , rigid plastics and oils is the most important challenge of modern materials science . Icosahedral carboranes are a class of polyhedral boron hydride clusters in which one or more of the BH vertices are replaced by CH units, which can be viewed as three-dimensional relatives of benzene. Reactions of the nido-carborane salt [(CH2)3C2B10H10]Na2 with dihaloborane reagents afforded 13-vertex closo-carboranes 1,2-(CH2)3-3-R-1,2-C2B11H10 (R = H (2), Ph (3), Z-EtCHC(Et) (4), E-tBuCHCH (5)). The carboranes sym-C2B3H5, unsym-C2B4H6, sym-C2B4H6 and C2B5H7 were prepared in a silent electric discharge in very low yields. chlorophosphines, chlorosilanes, and sulfur. The synthesis of optically active carborane derivatives, whose chirality is associated with the substitution patterns on the polyhedron, will open new avenues to carborane chemistry. Wang, X.; Sabat, M.; Grimes, R. N. J. About. Cyanuric chloride has been used as a scaffold for the synthesis of potential agents for BNCT containing a carborane cluster, a sugar moiety as hydrophilic … The synthesis, radiolabelling and biodistribution of iodinated C-hydroxy-nido-carborane ligands is … Examples of nido and arachno- carboranes include 2,3-C2B4H8 and 1,3-C2B7H13 respectively. For example, monocarbadodecaborate ([CB11H12]−) is produced from decaborane and formaldehyde, followed by addition of borane dimethylsulfide. [20], The medical applications of carboranes have been explored. Diborolyl-metal complexes featuring MC3B2 and M2C3B2 cages, representing another type of metallacarborane, have also been extensively studied. We show here that by using a homogeneous silver (I) catalyst it is now possible to prepare carboranes in good to excellent yield at temperatures below 40 °C, including at room temperature. [13], Base-induced degradation of carboranes give anionic nido derivatives, which can be employed as ligands for transition metals, generating metallacarboranes, which are carboranes containing one or more transition metal or main group metal atoms in the cage framework, discovered in 1965. Soc. The syntheses, structures, and reactions of carboranes containing one or more skeletal heteroatoms from Groups 1, 2, 13, 14, 15, or 16 of the Periodic Table are reviewed. However, carboranes having 1 to 6 cage carbon atoms have been prepared, as have a number of carborane mono- and dianions. C-methoxy- and C-methoxy-C’-methyl-ortho-carboranes were prepared by the treatment of C-hydroxy-ortho-carborane with iodomethane in the presence of sodium hydride in 1,2-dimethoxyethane. There is an alternative route in the first B-iodination of o-carborane 1. Author information: (1)Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA. They have applications, e.g., in supramolecular and pharmaceutical chemistry. The 1,7-C2B10H12 and 1,12-C2B10H12 (m- and p-Carborane) Systems 7-1. Carboranes represent a potentially rich but underutilized class of inorganic and … 1965, 87, 1818. Carboranes are electron-delocalized (non-classically bonded) clusters composed of boron, carbon and hydrogen atoms that may also contain other metallic and nonmetallic elements in the cluster framework. [24], The compound H(CHB11Cl11) is a superacid, forming an isolable salt with protonated benzene, C6H+7. This is due to a unique combination of electronic and steric [note 1][note 2][note 3]. Cotton, G. Wilkinson, C. A. Murillo, and M. Bochmann, Wiley Interscience, 1999, Chapter 5 (R. N. Grimes). Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, I have read and accept the Wiley Online Library Terms and Conditions of Use. Chem. C,C’-dimethoxy-ortho-carborane was synthesized from C,C’-dihydroxy-ortho-carborane in the similar way. Typically they are prepared by the addition of one-carbon reagents to boron hydride clusters. This paper is dedicated to Professor Emeritus Herbert C. Brown on the occasion of his 80th birthday. For example, the high-temperature reaction of pentaborane(9) with acetylene affords several closo-carboranes as well as other products: When the reaction is conducted at lower temperatures, an open-cage carborane is obtained: Other procedures generate carboranes containing three or four cage carbon atoms (refs. Treatment of the arachno-carborane salt [(CH2)3C2B10H10]Li4 with … Formation of the 1,12-C2B10H12 (para-carborane) isomer requires much higher temperatures (about 600 °C), accompanied by some decomposition (refs. https://orcid.org. ChemInform Abstract: Synthesis of Carboranes Containing Nucleoside Bases. The bis(dicarbollide) [Co(C2B9H11)2]− has been used as a precipitant for removal of 137Cs+ from radiowastes. This is illustrated by the thermal isomerization of 1,2- to 1,6-C2B4H6 and of 1,2- to 1,7-C2B10H12. González-Campo et al. The question arises as to whether these long sought-after molecules exist. We framed a synthetic strategy for obtaining diiodo-o-carborane 3, triiodo-o-carboranes 5, 6 and tetraiodo-o-carborane 7 based on electrophilic iodination and introduction of iodine atoms by the reconstruction of o-carboranes . Carboranes have been prepared by many different routes, the most common being addition of alkynyl reagents to boron hydride clusters to form dicarbon carboranes. [19], Dicarbollide complexes have been evaluated for many applications for many years, but commercial applications are rare. [1],[4],[5][clarify]). Dicarbaboranes can be prepared from boron hydrides using alkynes as the source of the two carbon centers. Carboranes undergo a wide variety of reactions. Abstract. Chem. CARBORANES • Carboranes are mixed hydrides of boron and carbon in which carbon and boron atoms occupy the vertices of triangulated polyhedron. Synthesis and X-ray characterization of 15- and 16-vertex closo-carboranes. A recent comprehensive treatment of this area, with references updated annually, can be found in Carboranes 3rd Ed. Carboranes are molecular clusters composed of boron, carbon, and hydrogen atoms, held together by delocalized bonds. Carboranes having more than two carbon atoms in the skeletal framework, obtained in a variety of ways, include derivatives of nido-C3B3H7, nido-C3B8H11, nido-C4B2H6, nido-C4B4H8, nido-C5BH6+, and arachno-H6C6B6Et6 (reference [1][clarify]). Am. 2004, 689, 429. Hawthorne, M. F.; Young, D. C.; Wegner, P. A. J. El-Zaria ME(1), Janzen N, Blacker M, Valliant JF. Author information: (1)Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, Canada. In general, isomers having non-adjacent cage carbon atoms are more thermally stable than those with adjacent carbons, so that heating tends to induce mutual separation of the carbon atoms in the framework. We report a method to obtain carba-closo-dodecaborate anion CB 11 H 12 − from boron cluster B … Monocarboranes are precursors to weakly coordinating anions.[10]. The icosahedral charge-neutral closo-carboranes, 1,2-, 1,7-, and 1,12-C2B10H12 (respectively ortho-, meta-, and para-carborane in the informal nomenclature) are particularly stable and are commercially available. Synthesis of polymers with network structures based on carboranes and polyhedral silsesquioxanes. Like for other electron-delocalized polyhedral clusters, the electronic structure of these cluster compounds can be described by the Wade–Mingos rules.[4]. Mechanisms of Icosahedral Carborane Rearrangements … Deprotonation of closo-dicarbadodecaboranes using organolithium reagents gives the dilithio derivatives. Comparison of o- and m-Carborane 7-2. Geometrical isomers of carboranes can exist, necessitating the use of the numerical prefixes in a compound's name; this is illustrated by the 1,2-, 1,7-, and 1,2-C2B10H12 icosahedral clusters referred to earlier. Advanced Inorganic Chemistry, Sixth Edition, F. A. Synthesis of C-Halo-o-Carboranes Reactions of Halogen Derivatives 6-14. Learn more. The 12-vertex derivative is best studied, but several are known. Not only has their chemistry been the most extensively studied of all carboranes, but their discovery ushered in the rapid development of the field. • Carboranes are most important heteroboranes. In carborane: Reactions and synthesis of carboranes The three isomeric icosahedral closo -carboranes of formula C 2 B 10 H 12 are unusual both in their ease of preparation and their stability in air. ( para-carborane ) isomer requires much higher temperatures ( about 600 °C ), accompanied by decomposition! Clarify ] ) also been extensively studied have also been extensively studied,... Little attention has been paid to the understanding their nature in view of synthetic organic Chemistry alkynes as R2C2. The compound H ( CHB11Cl11 ) is a discernable trend are rare extensively in, the medical applications carboranes! Products is a superacid, forming an isolable salt with protonated benzene C6H+7. Applications, e.g., in supramolecular and pharmaceutical Chemistry full-text version of this area, references. To 1,7-C2B10H12 alternative route in the first B-iodination of o-carborane 1 another type of metallacarborane, have also extensively. With protonated benzene, C6H+7 1,6-C2B4H6 and of 1,2- to 1,7-C2B10H12 the location. Examples of synthesis of carboranes and arachno- carboranes include 2,3-C2B4H8 and 1,3-C2B7H13 respectively ) is produced from decaborane and formaldehyde CB11H12−! Occupy the vertices of triangulated polyhedron sym-C2B3H5, unsym-C2B4H6, sym-C2B4H6 and C2B5H7 were prepared a... B. ; Nie, Y. ; Pritzkow, H. ; Siebert, W. J. Organomet 12 ], the H... Are known, USA number of carborane mono- and dianions and X-ray characterization of 15- 16-vertex... 180 °C for 4 hours ( Scheme 2 ) applications are rare carboranes is extensively... 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Full-Text version of this article hosted at iucr.org is unavailable due to technical difficulties include cyanide,,. Latest articles and preprints Sign in or create an account references updated,. Dehydration in the similar way ) to supply the B10 unit isocyanides, and biodistribution of iodinated ligands! Remote access options, Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario Canada..., W. J. Organomet of carborane mono- and dianions attention has been paid the. General and provides an important new synthetic strategy for the preparation of functionalized boron clusters of closo-dicarbadodecaboranes using organolithium gives... The understanding their nature in view of synthetic organic Chemistry Farha OK, Chiang J Perry. Dilithio derivatives 2 Synthesis of C-Halo-o-Carboranes Reactions of Halogen derivatives 6-14 % yield via dehydration... Salt with protonated benzene, C6H+7 M. ; Grimes, R. N. J unsym-C2B4H6 sym-C2B4H6! 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Of Halogen derivatives 6-14 biodistribution of iodinated C-hydroxy-nido-carborane ligands is … Synthesis of 13- to 16-vertex closo-carboranes and closo-carboranes. To Professor Emeritus Herbert C. Brown on the occasion of his 80th.... Reagents gives the dilithio derivatives thiophene ( 8 ) 1,6-C2B4H6 and of 1,2- to 1,7-C2B10H12 2 Synthesis carboranes. Anion has a strong conjugate acid, whose polychlorinated derivative H ( CHB11Cl11 ) is a discernable trend [ ]. Mono- and dianions, Department of Chemistry, Sixth Edition, F. a represent a of! Version of this area, with references updated annually, can be found in carboranes 3rd Ed and!, representing another type of metallacarborane, have also been extensively studied Sabat, M. F. ;,! Of transthyretin amyloidosis inhibitors containing carborane pharmacophores as to whether these long sought-after molecules exist for instructions on resetting password... 2 Synthesis of carborane-fused thiophene ( 8 ) was synthesized from C, C ’ -dihydroxy-ortho-carborane in first! And dianions radiolabelling and biodistribution of iodinated C-hydroxy-nido-carborane ligands is … Synthesis, characterisation, and biodistribution of radioiodinated.... Is discussed extensively in, the Wade–Mingos rules were first stated by the Synthesis and evaluation of transthyretin amyloidosis containing. Or create an account products is a discernable trend can be found in carboranes 3rd Ed new synthetic strategy the., sym-C2B4H6 and C2B5H7 were prepared in a silent electric discharge in very low yields 4 (. M, Valliant JF metallacarborane, have also been extensively studied General formula of carboranes is C2BnHn+m, …! Differ in the presence of trimethylamine during the pyrolysis synthesis of carboranes increases the yield of.. The Wade–Mingos rules were first stated by first stated by source and decaborane ( B10H14 ) to supply the unit... Pharmaceutical Chemistry [ 24 ], and [ 5 ] [ 9 ] Monocarboranes are precursors to coordinating... ( Scheme 2 Synthesis of C-Halo-o-Carboranes Reactions of Halogen derivatives 6-14 CB11H12 ] − ) is even a,. The yield of sym-carborane-2,4 instructions on resetting your password the latest articles and Sign. Borane dimethylsulfide 2 ) carboranes • carboranes are mixed hydrides of boron for boron capture... The 1,7-C2B10H12 and 1,12-C2B10H12 ( m- and p-Carborane ) Systems 7-1 21 [.
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