Journal
ORGANIC LETTERS
Volume 23, Issue 17, Pages 6911-6915Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02459
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Funding
- CHEFFPE [CHE124B]
- CHEGDCP from UCSD
- [CHE63CP]
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The newly synthesized cyclohexeno[3,4]cyclodec-1,5-diyne-3-ene can serve as a convenient model substrate for studying the reactivity of enediynes, with its p-dehydrobenzene diradical being trapable by nucleophiles in solution. The cyclization is the rate-limiting step, with a speed slightly slower than the parent substrate but faster than its benzene analogue.
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.
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