Journalartikel

Beyond Schmittel and Myers-Saito cyclizations: Rearrangements of 4-heteroatom-1,2-hexa-diene-5-ynes


AutorenlisteBui, BH; Schreiner, PR

Jahr der Veröffentlichung2003

Seiten4871-4874

ZeitschriftOrganic Letters

Bandnummer5

Heftnummer25

ISSN1523-7060

DOI Linkhttps://doi.org/10.1021/ol0360243

VerlagAmerican Chemical Society


Abstract
[GRAPHICS]The thermal rearrangements of 4-heteroatom-1,2-hexadiene-5-ynes (2) were studied at the BLYP/6-311+G*//BLYP/6-31G* level of theory. Cyclization of 2 to heteroatom-containing cyclopentadienyl structures (6) competes with the Claisen-type rearrangement to acyclic, allenic structures. Cyclizations to cyclobutene (4)- and cyclohexadiene (8)-derived heterocycles are not feasible as a result of high reaction barriers and lower-lying alternative pathways.



Zitierstile

Harvard-ZitierstilBui, B. and Schreiner, P. (2003) Beyond Schmittel and Myers-Saito cyclizations: Rearrangements of 4-heteroatom-1,2-hexa-diene-5-ynes, Organic Letters, 5(25), pp. 4871-4874. https://doi.org/10.1021/ol0360243

APA-ZitierstilBui, B., & Schreiner, P. (2003). Beyond Schmittel and Myers-Saito cyclizations: Rearrangements of 4-heteroatom-1,2-hexa-diene-5-ynes. Organic Letters. 5(25), 4871-4874. https://doi.org/10.1021/ol0360243



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