Year: 2012
Type: article
Abstract: 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.
Source: ARKIVOC
Institution: The University of Texas at San Antonio
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W2542984373