73557-66-1Relevant academic research and scientific papers
Selective Vicinal Diiodination of Polycyclic Aromatic Hydrocarbons
Bolte, Michael,Jin, Tao,John, Alexandra,Kaehler, Tanja,Lerner, Hans-Wolfram,Wagner, Matthias
supporting information, p. 5847 - 5851 (2020/09/09)
Vicinally diiodinated polycyclic aromatic hydrocarbons (I2-PAHs) are accessible from the corresponding diborylated B2-PAHs through boron/iodine exchange. The B2-PAHs have been prepared via twofold electrophilic borylation reactions templated by a vicinally disilylated benzene. Our protocol is applicable to fluorenes, acenes, annulated acenes, oligoaryls, and even [5]helicene. Using B2-naphthalene as the example, we have shown that the reaction scope can, in principle, be expanded to include the synthesis of vicinally dibrominated and dihydroxylated PAHs. The usefulness of the building blocks provided by our method in the field of optoelectronic materials was demonstrated by the successful conversion of I2-fluoranthene to the analogous doubly alkynylated fluoranthene emitter.
The regioselective generation of arynes from polyhalogenobenzenes. An improved synthesis of syn- and anti-1,4,5,8,9,12-hexahydro-1,4:5,8:9,12-triepoxytriphenylene
Raymo, Francisco,Kohnke, Franz H.,Cardullo, Francesca,Girreser, Ulrich,Fraser Stoddart
, p. 6827 - 6838 (2007/10/02)
The halogenated benzenes, 1,2,4,5-tetrabromobenzene 6, hexabromobenzene 9, p-dichlorotetrabromobenzene 11, and 1,2-dibromo-4,5-dichlorobenzene 12, were investigated as 1,3-bis-, 1,4-bis-, and 1,3,5-tris-aryne precursors by using alkyllithiums and alkali m
THE DILITHIATION MECHANISM IN THE REACTIONS OF POLYHALOARENES AS DI-ARYNE EQUIVALENTS
Hart, Harold,Nwokogu, Godson C.
, p. 5721 - 5724 (2007/10/02)
The preparation of certain 1,4-dilithio-tetrahaloarenes is described; they react with electrophiles at low temperatures or form arynes at higher temperatures.
ATTEMPTS TO POLYLITHIATE TETRABROMOARENES. THE COMPATIBILITY OF METHYL SULFATE AND BUTYLLITHIUM
Nwokogu, Godson C.,Hart, Harold
, p. 5725 - 5726 (2007/10/02)
Tetrabromo-o- and p-dichlorobenzenes are only dilithiated, even with excess n-butyllithium, although more than two bromines are replaced by methyl groups when such solutions are treated with methyl sulfate.
Alkyl Nitrite-Metal Halide Deamination Reactions. 7. Synthetic Coupling of Electrophilic Bromination with Substitutive Deamination for Selective Synthesis of Multiply Brominated Aromatic Compounds from Arylamines
Doyle, Michael P.,Lente, Michael A. van,Mowat, Rex,Fobare, William F.
, p. 2570 - 2575 (2007/10/02)
Aromatic amines undergo substitution with copper(II)bromide that is in competition with substitutive deamination when these reactions are performed with tert-butyl nitrite.Except for the exceptionally reactive 4-substituted 1-aminonaphthalenes,which undergo selective bromine substitution at the 1- and 2-positions in relatively high isolated yields,rates for oxidative bromination and substitutive deamination are not sufficiently different that selective multiple bromination can be achieved.Oxidative bromination of N,N-dimethylaniline by copper(II)bromide occurs with partial dealkylation,and nitration products are observed from reactions performed with copper(II)bromide and tert-butyl nitrite.Implications of these results for the successful utilization of copper(II)bromide/tert-butyl nitrite combinations in substitutive deamination reactions of aromatic amines are discussed.Multiply brominated aromatic compounds are produced from aromatic amines in high yield through treatment of the aromatic amine with the combination of molecular bromine and catalytic quantities of copper(II)bromide and,following a normally brief time delay,with tert-butyl nitrite.All unsubstituted aromatic ring positions ortho and para to the amino group,as well as the position of the amino group,are substituted by bromine.The only observed byproducts from use of this procedure (usually 2percent yield) are the partially brominated benzene derivatives.
