Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5218545 | Tetrahedron | 2013 | 7 Pages |
Abstract
We developed a novel synthetic method for allenyl spiro[4.5]cyclohexadienone derivatives based on a base-promoted intramolecular ipso-Friedel-Crafts addition of phenols to propargyl bromides. The present spirocyclization proceeded in a CH2Cl2-tert-BuOH mixed solvent system using potassium tert-butoxide as the base, and produced the corresponding spiro[4.5]cyclohexadienone derivatives with an allene motif in up to 99% yield. This-type allenyl spirocycle was also accessible through Pd-catalyzed intramolecular ipso-Friedel-Crafts alkylation when a propargyl carbonate derivative with a naphthol unit was used as a substrate. Acid-promoted skeletal rearrangement of the reaction adducts was also examined.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Tetsuhiro Nemoto, Riliga Wu, Zengduo Zhao, Takuya Yokosaka, Yasumasa Hamada,