Octakis naphthalenes

Perfluorodecalin is transformed to octakis(phenylthio)naphthalene by phenyl thiolate in dipol ar aprotic solvents The crucial first step of this reaction may involve an elimination of the tertiary fluorine atoms, which would lead to a symmetric perfluorobicyclic olefin as an intermediate [65] (equation 58). 

Thermolysis of compound 47 in the presence of benzophenone or naphthalene at 200-220 °C provides two products, 2,2,4,4,5,5-hexakis(2,6-diethylphenyl)pentastanna-[l,l,l]propellane, 49, and octakis(2,6-diethylphenyl)octastannacubane89, 50, as well as traces of R SnSnRj. 

Despite the well-known chemical stability of perfluorinated aliphatic compounds, pcr-fluorinated Decalin can be reacted w ith alkane- or arenethiols under very mild conditions yielding octakis(alkylsulfanyl)- or octakis(arylsulfanyl)naphthalenes 2.6 The reaction starts at the tertiary carbon atoms where the C — F bond is the weakest, since perfluorocyclohexane does not react under similar conditions, but perfluorocyclohexene does.6... 

Octakis(alkylsulfanyl)- or Octakis(arylsulfanyl)naphthalenes 2 General Procedure 6... 

Explanation 70 is a big surprise. On heating for weeks at 90°C with a large excess of sodium salt of a hydroxy compound in A.iV -dimethyl-imidazolid-2-one, all fluorine atoms are replaced by the residues of the hydroxy compounds such as m-cresol, 2-naphthol, or 2-hydroxytetralin. Compound L is octakis(alkoxy)- or octakis(aryloxy)naphthalene [98]. 

Thermolysis of hexakis (2,6-diethylphenyl)cyclotristannane (21) in naphthalene at 200-220°C gave red octakis(2,6-diethylphenyl)octastana-cubane (22) in 0.76% yield together with dark blue violet pentastanna-... 

The successful synthesis of octakis(phenylthio)- 70a59, octakis(aryloxy)- 70b60 and octapyrrolyl naphthalenes 70c61 has demonstrated a possibility of multiple substitution of fluorine atoms in octafluoronaphthalene (OFN) under the action of relatively mild nucleophiles. This approach has been recently tested for the preparation of polykis(dialkyl-amino)naphthalenes. 

Synthesis of octakis 3-[(2-hydroxYethYljdimethylammonio]propyl octasiisesquioxane chloride via nucleophilic substitution 148 Synthesis of heptaisobutyl[2- 4-(1-naphthyljphenYl ethenyl]octasilsesquioxane via siiyiative coupiing of monovinylheptaisobutylsilsesquioxane with T(4-vinylphenyl)naphthalene 149... 

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