Progress on the synthesis of 1,2,3,5,9-cyclodecapentaen-7-yne and supporting studies

Citation

Yang, Maximillian Y. (1992) Progress on the synthesis of 1,2,3,5,9-cyclodecapentaen-7-yne and supporting studies. Master's thesis, California Institute of Technology. http://resolver.caltech.edu/CaltechTHESIS:10042011-102102178

Abstract

Progress on the synthesis of 1,2,3,5,9-cyclodecapentaen-7-yne (1), a compound structurally related to both (Z)-1,2,4-heptatrien-6-yne and the activated core of neocarzinostatin chromophore, is reported. The novel compound 1 is of theoretical interest as an example of a monocyclic 10-membered ring that fulfills the aromaticity requirements of Hückel's rule. The alcohol 24, envisioned to serve as a possible precursor to 1, has been synthesized.

In related, collaborative studies, 1-bromo-4-trimethylsilylnaphthalene, 1-bromo-5-trimethylsilylnaphthalene, 2-bromo-7-trimethylsilylnaphthalene, 1-chloro- 4-trimethylsilylnaphthalene, 1-chloro-5-trimethylsilylnaphthalene, and 2-chloro-7- trimethylsilylnaphthalene have been synthesized. These compounds will be used in gas-phase studies as precursors to the corresponding naphthalene biradicals. These studies will determine the heat of formation of each corresponding naphthalene biradical.

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