52158-48-2Relevant articles and documents
Utilization of Donor–Acceptor Interactions for the Catalytic Acceleration of Nucleophilic Additions to Aromatic Carbonyl Compounds
Uchikura, Tatsuhiro,Ono, Kosuke,Takahashi, Kohei,Iwasawa, Nobuharu
supporting information, p. 2130 - 2133 (2018/02/06)
A conceptually new method for the catalytic electrophilic activation of aromatic carbonyl substrates, by utilizing donor–acceptor interactions between an electron-deficient macrocyclic boronic ester host ([2+2]BTH-F) and an aromatic carbonyl guest substrate, was realized. In the presence of a catalytic amount of [2+2]BTH-F, dramatic acceleration of the nucleophilic addition of a ketene silyl acetal towards either electron-rich aromatic aldehydes or ketones was achieved. Several control experiments confirmed that inclusion of the aromatic substrates within [2+2]BTH-F, through efficient donor–acceptor interactions, is essential for the acceleration of the reaction.
PARTIALLY FLUORINATED HETEROCYCLIC COMPOUNDS PART 28. THE HYDROLYSIS OF 1,3,4,5,6,7,8-HEPTAFLUORO-2-NAPHTHYLIDENERHODANINE TO FORM RING-FUSED THIOPHENES. A SIGNIFICANT PROPORTION OF A LINEAR NAPHTHOTHIOPHENE DERIVATIVE ACCOMPANYING AN ANGULAR NAPHTHOTHIOPHENE DERIVATIVE
Brooke, Gerald M.,Meara, Jeremy M.
, p. 229 - 242 (2007/10/02)
1,3,4,5,6,7,8-Heptafluoronaphthalene-2-carbaldehyde (7), prepared via a Grignard reaction from 2-bromo-1,3,4,5,6,7,8-heptafluoronaphthalene (9) with N-methylformanilide, reacted with rhodanine to give 1,3,4,5,6,7,8-heptafluoro-2-naphthylidenerhodanine (5).Hydrolysis of (5) with base gave a mixture of 4,5,6,7,8,9-hexafluoronaphthopthiophene-2-carboxylic acid (11) and 4,5,6,7,8,9-hexafluoronaphthothiophene-2-carboxylic acid (12) resulting from the intermediate thiolate (6) displacing fluorine at sites 3 and 1 in the naphthalene ring in the ratio 22:78 respectively, which represents a significantly high portion of the linearly cyclised product accompanying the angularly cyclised product.Decarboxylation of the mixture of (11) and (12) gave 4,5,6,7,8,9-hexafluoronaphthothiophene (13) and 4,5,6,7,8,9-hexafluoronaphthothiophene (14) respectively, while treatment of the mixture (11) and (12) with diazomethane gave an inseparable mixture of the methyl 2-carboxylates (15) and (16) respectively.