Chemistry of Boranes. XIX.1 Derivative Chemistry of B10H10-2 and B12H12-2

Knoth, W. H.; Sauer, J. C.; England, David C.; Hertler, W. R.; Muetterties, E. L.

doi:10.1021/ja01073a015

Cited by 106 publications

(72 citation statements)

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“…Reaction of closo-dodecaborate anion 1 with hydroxylamine-O-sulfonic acid results in the formation of small quantities (<10%) of the desired 1,12-diamine 138,139 , while the same reaction for the ten-vertex analog 7 yields equatorial diamines only 138 . Similar results are obtained for hydroxylation reactions with amides and sulfones 140,141 .…”

Section: Boron Substitutionsupporting

confidence: 84%

“…H 12 ] 2-with other electrophiles proceed with the formation of predominately meta (1,7-) isomers and the desired para (1,12-) isomers are minor products which are difficult to detect and isolate 132,140,153 . Similarly, other electrophilic substitution reactions of [B 10 H 10 ] 2-yield either mixtures of apical/equatorial or exclusively equatorial 6 products: e.g.…”

Section: Reactions Of [B 12mentioning

confidence: 99%

“…Similarly, other electrophilic substitution reactions of [B 10 H 10 ] 2-yield either mixtures of apical/equatorial or exclusively equatorial 6 products: e.g. reaction with halogens 158 , carbonyl chlorides 132,140,158,159 , protonated MeCN (ref. 160 ), and N,N-dimethylthioformamide 152 .…”

Section: Reactions Of [B 12mentioning

confidence: 99%

“…Baeyer-Villiger oxidation of closo-borane ketones has not been investigated in detail except in the case of derivatives of [B 12 H 12 ] 2-and [B 10 H 10 ] -, which provide access to the corresponding B-hydroxy derivatives 132,140 . Other routes to the B-hydroxy compounds include hydrolysis of amide and sulfone adducts to 1 and 7 (ref.…”

Section: N Phmentioning

confidence: 99%

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Four Decades of Organic Chemistry of closo-Boranes: A Synthetic Toolbox for Constructing Liquid Crystal Materials. A Review

Kaszyński

1999

Collect. Czech. Chem. Commun.

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Introduction and transformations of organic functional groups to ten- and twelve-vertex closo-boranes and heteroboranes is reviewed in the context of preparation of liquid crystalline compounds. The review, containing 198 references, is designed as a synthetic manual for materials chemists and focuses on methods for engineering molecules with elongated shapes and variable dipole moments. Several underdeveloped aspects of closo-borane chemistry are identified.

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Section: Boron Substitutionsupporting

confidence: 84%

Section: Reactions Of [B 12mentioning

confidence: 99%

Section: Reactions Of [B 12mentioning

confidence: 99%

Section: N Phmentioning

confidence: 99%

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Four Decades of Organic Chemistry of closo-Boranes: A Synthetic Toolbox for Constructing Liquid Crystal Materials. A Review

Kaszyński

1999

Collect. Czech. Chem. Commun.

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“…1,2 This therapy is based on the capture reaction of low-energy (0.025 eV) thermal neutrons using nonradioactive boron-10 ( 10 B), which produces a particles and 7 Li nuclei with high energy, as follows:…”

Section: Introductionmentioning

confidence: 99%

Boron neutron capture therapy assisted by boron-conjugated nanoparticles

Sumitani

Nagasaki

2012

Polym J

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For high-performance boron neutron capture therapy (BNCT), core-shell-type biodegradable nanoparticles possessing boron clusters in their cores are designed to improve their accumulation tendency in the tumor region. The copolymerization of styrene carrying carborane with a poly(ethylene glycol)-block-poly(lactide) copolymer (PEG-b-PLA) that possesses an acetal group at its PEG end and a methacryloyl group at its PLA end (acetal-PEG-b-PLA-MA) was performed in an aqueous medium. As the acetal-PEG-b-PLA-MA forms a polymeric micelle in an aqueous medium, the carborane monomer in the hydrophobic core is solubilized, and the carborane in the core of the micelle is given covalent conjunction. Two carborane compounds, carborane with a mono-vinylbenzyl group [1-(4-vinylbenzyl)-closo-carborane (VB-carborane)] and carborane with di-vinylbenzyl groups [1,2-bis(4-vinylbenzyl)-closo-carborane ((VB) 2 -carborane)], were newly prepared and employed for the core polymerizations. The encapsulation efficiency of the VB-carborane in the micelles is much higher than that of the (VB) 2 -carborane. This improved efficiency is most likely caused by the interaction of the hydrogen bonding of the VB-carborane with the polymer micelle matrix, while no hydrogen bonding sites remain in the case of the (VB) 2 -carborane. The obtained corepolymerized and boron-conjugated micelles (PM, which were prepared from VB-carborane) showed extremely high stability under physiological conditions, which suppressed the leakage of boron compounds owing to the existence of the covalent bonds. The accumulation of the PM (7.2 ID% per g) in tumors is much higher than that of the non-polymerized micelles (NPM) (0.7 ID% per g) under the same conditions (at 24 h after injection) because of the enhanced stability of the micelles under physiological conditions. In addition, thermal neutron irradiation experiments indicated significant suppression of the growth of tumor volume in tumor-bearing mice treated with the PM. It is important to note that the PM administered via intravenous injection were excreted almost completely from the major organs, except for the tumor, after a week. Therefore, these boronconjugated micelles represent a promising approach to the creation of a novel boron carrier for BNCT.

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