Journal article

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


Authors list: Bui, BH; Schreiner, PR

Publication year: 2003

Pages: 4871-4874

Journal: Organic Letters

Volume number: 5

Issue number: 25

ISSN: 1523-7060

DOI Link: https://doi.org/10.1021/ol0360243

Publisher: American 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.



Citation Styles

Harvard Citation style: Bui, 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 Citation style: Bui, 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


Last updated on 2025-21-05 at 13:32