Thallium in organic synthesis. XXII. Electrophilic aromatic thallation using thallium(III) trifluoroacetate. Simple synthesis of aromatic iodides

McKillop, Alexander; Hunt, J. D.; Zelesko, Michael J.; Fowler, Joanna S.; Taylor, Edward C.; McGillivray, G.; Kienzle, Frank

doi:10.1021/ja00748a029

Cited by 132 publications

(34 citation statements)

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“…The results with mercury and thalliun~ salts are very interesting, since even though fluorine is the most reactive halogen, it fluorinates these compounds very poorly, or not at all, in contrast to the results obtained by treating these same compounds with other halogens (2,19,21).…”

Section: Resultsmentioning

confidence: 90%

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The cleavage of aryl-metal bonds by elemental fluorine: synthesis of aryl-fluorides

Adam¹,

Berry²,

Hall³

et al. 1983

Can. J. Chem.

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The reaction of elemental fluorine with phenyl derivatives of tin, lead, germanium, silicon, mercury, and thallium has been studied with the aim of developing a general method for labelling aromatic compounds with radioactive 18F. Rapid synthesis of fluorobenzene was achieved in varying chemical yields up to 70%, depending largely upon the metal substrate used, with aryl–tin compounds giving the highest yields. Radiochemical yields are also given for the synthesis of 18F-fluorobenzene from the cleavage of aryl–tin bonds with 18F-F2.

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Section: Resultsmentioning

confidence: 90%

“…phcnylmcrcury acctatc, and phenyl~nercury chloride were purchascd from Alfa Products, Danvers, MA, and tctraphenylgerman~um and tetrilphcnylsilane were purchascd from PCR Research Chcmlcals lnc., Gaincsv~lle, FL. Phenylthallium bis-trifluoroacetatc (21). phenylmercury trifluoroacetate (21.…”

Section: Methodsmentioning

confidence: 99%

The cleavage of aryl-metal bonds by elemental fluorine: synthesis of aryl-fluorides

Adam¹,

Berry²,

Hall³

et al. 1983

Can. J. Chem.

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“…The methods for iodination have been used previously for indolealkylamine [4] and phenethylamines [4] using thallium trifluoroacetate as specific oxidizing agent of molecular iodine for iodination of aromatic compounds [5].…”

Section: Iodinationmentioning

confidence: 99%

A Facile High-Yield Synthesis of [10 B]-8-Dihydroxyboryl Harmine, a Potential Agent for Boron Neutron Capture Therapy

Sintas¹,

Macareno²,

Vitale³

2000

Molecules

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The resurgence of interest in Boron Neutron Capture Therapy (BNCT) as a treatment for malignant lesions has resulted in the synthesis of numerous boron compounds as candidates for clinical use. BNCT is a selective radiotherapy using boron-10 which absorbs thermal neutrons and releases high Linear Energy Transfer (LET) alpha particles by 10 B (n, α) 7 Li reaction. The alpha radiation kills cells in the range of 5-9 µm from the site of the α generation. Therefore, it is theoretically possible to kill tumor cells without affecting adjacent healthy tissues, if 10 B-compounds could be selectively deliv- . They have a well know brain distribution, so these compounds, labeled with 10 B are potential agents for BNCT. A general synthetic method has been developed for the rapid and efficient production of boronated Harmine. Results And Discussion IodinationThe methods for iodination have been used previously for indolealkylamine [4] and phenethylamines [4] using thallium trifluoroacetate as specific oxidizing agent of molecular iodine for iodination of aromatic compounds [5]. BoronationWe used the condensation of the Grignard reagent from 8-I-Harmine with trimethylborate. This method was previously used [6] for preparation of phenol from phenylbromide and trimethylborate with formation of phenylboronic acid as intermediate and for preparation of boronic analogue of cho-

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“…Recrystallization from 10% acetone in ethanol yielded 2.85 g (5. 75 The mother liquor obtained from recrystallization contained a mixture of the 5,5'-dinitro and the 3,5"-dinitro isomers as evident from NMR and HPLC analyses.…”

Section: Attempted Synthesis Of 22'-diiodo-55'-dinitrobiphenyl By Nmentioning

confidence: 99%

“…After solvent removal, the residue *was recrystallized from hexane-ether to yield 8. 75 The aqueous phase left behind was acidified and extracted with 3 X 100 ml of ether. The combined ethereal fractions were washed with 100 ml of water, dried over anhydrous magnesium sulfate and concentrated to a white solid.…”

mentioning

confidence: 99%

Chemistry, Characterization and Processing of IMC Curing Polymers.

Lau¹

1983

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Thallium in organic synthesis. XXII. Electrophilic aromatic thallation using thallium(III) trifluoroacetate. Simple synthesis of aromatic iodides

Cited by 132 publications

References 0 publications

The cleavage of aryl-metal bonds by elemental fluorine: synthesis of aryl-fluorides

The cleavage of aryl-metal bonds by elemental fluorine: synthesis of aryl-fluorides

A Facile High-Yield Synthesis of [10 B]-8-Dihydroxyboryl Harmine, a Potential Agent for Boron Neutron Capture Therapy

Chemistry, Characterization and Processing of IMC Curing Polymers.

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