New Syntheses of Cyclopentapyrene 3,4-Oxide and 4-Pyrenylacetic Acid

Article abstract of DOI:10.1021/jo00296a065

New syntheses of cyclopentapyrene 3,4-oxide (CPPE) and 4-pyrenylacetic acid, a key intermediate in the synthesis of cyclopentapyrene and CPPE, are described starting from 1,2,3,6,7,8-hexahydropyrene. 4-Pyrenylacetic acid is prepared from the corresponding alcohol, 2-(4-pyrenyl)ethanol, by applying two mild oxidation reactions. 4-Pyrenylacetaldehyde was obtained by N-chlorosuccinimide dimethyl sulfide oxidation, and this was converted smoothly to the desired 4-pyrenylacetic acid by silver oxide oxidation, an approach that has potential for a new route to arylacetic acids from arylethanols.The epoxide CPPE is prepared by cyclization of the 3,4-trans-dihydroxycyclopentapyrene via its monotosylate, prepared in situ, with powdered sodium hydroxide.