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A rare alder-ene cycloisomerization of 1,6-allenynes

Joyce, LM, Drew, MA, Tague, AJ, Thaima, T, Gouranourimi, A, Ariafard, A ORCID: 0000-0003-2383-6380, Pyne, SG and Hyland, CJT 2022 , 'A rare alder-ene cycloisomerization of 1,6-allenynes' , Chemistry - A European Journal, vol. 28, no. 12 , pp. 1-5 , doi: 10.1002/chem.202104022.

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Abstract

Thermally induced cycloisomerization reactions of 1,6-allenynes gives α-methylene-γ-lactams via intramolecular Alder-ene reactions. The mechanism is supported by computational and deuterium labelling studies. This thermal, non-radical method enables the discovery of a hitherto unknown route that proceeds via a divergent mechanism distinct from the previous [2+2] cycloisomerization manifold.

Item Type: Article
Authors/Creators:Joyce, LM and Drew, MA and Tague, AJ and Thaima, T and Gouranourimi, A and Ariafard, A and Pyne, SG and Hyland, CJT
Keywords: DFT calculations, cycloisomerization, allene
Journal or Publication Title: Chemistry - A European Journal
Publisher: Wiley-V C H Verlag Gmbh
ISSN: 0947-6539
DOI / ID Number: 10.1002/chem.202104022
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© 2021 Wiley-VCH GmbH

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