A Claisen rearrangement route to novel electron-rich perylene dyes

作者：Baffoe Djan; Smith Terrill D; Penick Mark A; Mahindaratne Mathew P D; Brancaleon Lorenzo; Negrete George R^*

来源：ARKIVOC, 2012, 112-118.

• Perylene
• Claisen rearrangement
• aromatization
• polycyclic aromatic hydrocarbon

A combined tandem Friedel-Crafts annulation/Claisen rearrangement strategy was developed for the preparation of tetrasubstituted perylenes. Diallyloxyoctahydroperylene was prepared from commercially available 1,2,3,4-tetrahydronaphth-1,5-diol and oxidized with chloranil to the perylene analogue. Claisen rearrangement followed to the novel 2,8-diallylperylene-3,9-diol, which was acylated in situ to the corresponding dioctanoyl ester. These results show that allyloxyperylene undergoes Claisen rearrangement efficiently, while partially hydrogenated analogue generates multiple products under identical conditions.

• 出版日期2012