New syntheses of cyclopenta(cd)pyrene 3,4-oxide and 4-pyrenylacetic acid

Journal Article · Fri Apr 27 04:00:00 UTC 1990 · Journal of Organic Chemistry; (United States)

DOI:https://doi.org/10.1021/jo00296a065· OSTI ID:6015629

Sahali, Y; Skipper, P L; Tannenbaum, S R ^[1]

---

1. Massachusetts Inst. of Tech., Cambridge (United States)

New syntheses of cyclopenta(cd)pyrene 3,4-oxide (CPPE) and 4-pyrenylacetic acid, a key intermediate in the synthesis of cyclopenta(cd)pyrene and CPPE, as 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-dihydroxycyclopenta(cd)pyrene via its monotosylate, prepared in situ, with powdered sodium hydroxide.

• OSTI ID: 6015629
• Journal Information: Journal of Organic Chemistry; (United States), Journal Name: Journal of Organic Chemistry; (United States) Vol. 55:9; ISSN JOCEA; ISSN 0022-3263
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALKALI METAL COMPOUNDS
AROMATICS
BIOLOGICAL EFFECTS
CARBON
CARBON BLACK
CARBOXYLIC ACIDS
CHALCOGENIDES
CHEMICAL PREPARATION
CHEMICAL REACTIONS
CONDENSED AROMATICS
ELEMENTS
EXPERIMENT PLANNING
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXIDES
METABOLITES
MUTAGENS
NONMETALS
ORGANIC ACIDS
ORGANIC COMPOUNDS
OXIDATION
OXIDES
OXYGEN COMPOUNDS
PLANNING
POLYCYCLIC AROMATIC HYDROCARBONS
SILVER COMPOUNDS
SILVER OXIDES
SODIUM COMPOUNDS
SODIUM HYDROXIDES
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS