Well-defined, rigid molecular domes are obtained via substitution of the chlorine atoms of hexachlorobenzotrinorbornadiene syn-3, efficiently synthesized in 1:2 ratio along with its antiisomer by CuTC-promoted cyclotrimerization of 3-bromo-2-tri-methylstannylnorbornadiene 8. The three dichlorovinyl functions at the edge of syn-3 are displaced by sulfur nucleophiles and Grignard reagents with Ni(II)Cl2dppe as catalyst, gaining the persubstituted vinyl sulfides 9 and 10, and persubstituted methyl 12 and phenylethynyl 13.
Tris-annelated benzenes selectively perfunctionalized on one side only: Hexachlorobenzotrinorbornadiene as a versatile scaffold for the construction of molecular domes / Borsato, Giuseppe; Brussolo, Stefania; Crisma, Marco; De Lucchi, Ottorino; Lucchini, Vittorio; Zambon, Alfonso. - In: SYNLETT. - ISSN 0936-5214. - 7(2005), pp. 1125-1128. [10.1055/s-2005-865215]
Tris-annelated benzenes selectively perfunctionalized on one side only: Hexachlorobenzotrinorbornadiene as a versatile scaffold for the construction of molecular domes
ZAMBON, Alfonso
2005
Abstract
Well-defined, rigid molecular domes are obtained via substitution of the chlorine atoms of hexachlorobenzotrinorbornadiene syn-3, efficiently synthesized in 1:2 ratio along with its antiisomer by CuTC-promoted cyclotrimerization of 3-bromo-2-tri-methylstannylnorbornadiene 8. The three dichlorovinyl functions at the edge of syn-3 are displaced by sulfur nucleophiles and Grignard reagents with Ni(II)Cl2dppe as catalyst, gaining the persubstituted vinyl sulfides 9 and 10, and persubstituted methyl 12 and phenylethynyl 13.
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