The thermal C2–C6/[2 + 2] cyclisation of enyne-allenes: Reversible diradical formation

Mehmet Emin Cinar; Chandrasekhar Vavilala; Jian Fan; Michael Schmittel

doi:10.1039/C0OB01275K

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Organic & Biomolecular Chemistry

Issue 10, 2011

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The thermal C²–C⁶/[2 + 2] cyclisation of enyne-allenes: Reversible diradical formation

Mehmet Emin Cinar , Chandrasekhar Vavilala , Jian Fan and Michael Schmittel

Org. Biomol. Chem., 2011,9, 3776-3779

DOI: 10.1039/C0OB01275K
Received 30 Dec 2010, Accepted 07 Mar 2011
First published on the web 07 Mar 2011
This article is part of the collection: Free Radical Chemistry special themed issue in memory of Athel Beckwith

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New enyne-allenes, structurally designed toward the thermal C²–C⁶/[2 + 2] cyclisation mode, were prepared and characterised, one of them even by X-ray crystallography. The mechanism of their transformation to formal [2 + 2] cycloadducts was interrogated by trapping experiments and DFT computations. The results support a stepwise mechanism that involves the reversible formation of the C²–C⁶ diradical intermediate.