A novel hydrocarbon, 8,10-dimethylidenetricyclo[7.1.1.0(2,7)]undeca-2,4,6-triene: Synthesis of benzopinane skeleton via Di-pi-methane rearrangement of benzonorbornadiene system

Date

1998-01-01

Author

Altundas, A
Akbulut, N
Balcı, Metin

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The [4 + 2] cycloadduct 17 of 2,3-dimethylidene-1,2,3,4-tetrahydro-1,3-methanonaphthalene and 4-phenyl-4H-1,2,4-triazole-3,5-dione (PTAD) was subjected to a tripler-sensitized di-pi-methane rearrangement. Hydrolysis of the resulting urazol 18 gave the hydrocarbon 7. Hydrolysis of 18 at lower base concentrations led to isomeric stable semicarbazides 24 and 25, which were submitted NiO2 or MnO2, oxidation, to give the target compound 7, and oxidation products 26 and 27.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis

URI

https://hdl.handle.net/11511/57532

Journal

HELVETICA CHIMICA ACTA

DOI

https://doi.org/10.1002/hlca.19980810504

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

A. Altundas, N. Akbulut, and M. Balcı, “A novel hydrocarbon, 8,10-dimethylidenetricyclo[7.1.1.0(2,7)]undeca-2,4,6-triene: Synthesis of benzopinane skeleton via Di-pi-methane rearrangement of benzonorbornadiene system,” HELVETICA CHIMICA ACTA, pp. 828–836, 1998, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57532.