| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1324531 | Journal of Organometallic Chemistry | 2011 | 6 Pages |
Highly functionalized ferrocenyl-substituted phenols were prepared by cyclization of masked or free dianions with 1,3-dielectrophilic 1-η5-ferrocenyl-3,3-bis(methylthio)prop-2-en-1-ones. While the cyclizations of 1,3-bis(silyloxy)-1,3-butadienes (masked dianions) proceed by initial 1,2-addition, the reactions of free 1,3-dicarbonyl dianions proceed by initial 1,4-addition. Therefore, both regioisomeric ferrocenylphenols are available from one and the same electrophile dependent on the type of nucleophile and reaction conditions employed. The reactions reported represent the first examples of the application of formal [3 + 3] cyclizations to the synthesis of organometallic compounds.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Highly functionalized ferrocenyl-substituted phenols were prepared. ► Different regioselectivity was observed for cyclizations of cyclizations of 1,3-bis(silyloxy)-1,3-butadienes (masked dianions) and free 1,3-dicarbonyl dianions. ► First examples of the application of formal [3 + 3] cyclizations to the synthesis of organometallic compounds.
