Cyclohexeno[3,4]cyclodec-1,5-diyne-3-ene: A Convenient Enediyne

Autor:	Annadka Shrinidhi, Charles L. Perrin
Rok vydání:	2021
Předmět:	Diradical Chemistry Organic Chemistry chemistry.chemical_element Biochemistry Nucleophile Computational chemistry Chemical Sciences Enediyne Reactivity (chemistry) Physical and Theoretical Chemistry Carbon Ene reaction
Zdroj:	Organic letters, vol 23, iss 17
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.1c02459
Popis:	Enediynes are widely studied to understand their cycloaromatization and the trapping of the resulting p-dehydrobenzene diradical. However, few model substrates are known, and they are hard to synthesize and difficult to handle. Herein we report cyclohexeno[3,4]cyclodec-1,5-diyne-3-ene as a convenient model for studying the reactivity of enediynes. It can be easily synthesized from 1,2-diethynylcyclohexene and 1,4-diiodobutane. It is a solid that is stable at room temperature. In solution the p-dehydrobenzene diradical derived from its cycloaromatization can be trapped by nucleophiles. The rate-limiting step is the cyclization, which is slightly slower than that of the parent cyclodec-1,5-diyne-3-ene but faster than that of its benzo analogue, consistent with the distances between the reacting carbon atoms.
Databáze:	OpenAIRE
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