Clar Reaction of 7H-benz[de]anthracen-7-one: Isolation and Identification of Tetrabenzo[a,cd,lm,o]perylene | Health & Environmental Research Online (HERO)

Health & Environmental Research Online (HERO)

Print Feedback Export to File

This record has one attached file:

Citation
Tags

HERO ID

2672831

Reference Type

Journal Article

Title

Clar Reaction of 7H-benz[de]anthracen-7-one: Isolation and Identification of Tetrabenzo[a,cd,lm,o]perylene

Author(s)

Ehrenhauser, FS; Wornat, MJ

Year

2011

Is Peer Reviewed?

Journal

Polycyclic Aromatic Compounds
ISSN: 1040-6638
EISSN: 1563-5333

Volume

Issue

Page Numbers

123-142

DOI

10.1080/10406638.2011.576304

Web of Science Id

WOS:000299706700001

Abstract

The Clar reaction of 7H-benz[de]anthracen-7-one (20) was reinvestigated as a source for C34H18 polycyclic aromatic hydrocarbons (PAH). The utilization of a ternary sodium chloride/potassium chloride/zinc chloride melt with zinc dust as reducing agent yielded tetrabenzo[a,cd,j,lm]perylene (11) (10.7% yield), dibenzo[a, cd]naphtho[1,8-jk]perylene (16) (10.2% yield), and dibenzo[a, cd] naphtho[3,2,1-lm]perylene (14) (7.4% yield) as main products. Tetrabenzo[a, cd, lm, o] perylene (26) as a minor product of the Clar reaction was purified via semi-preparative high performance liquid chromatography, and its unequivocal identification was demonstrated through NMR data and a microscale-cyclization reaction.

Keywords

C(34)H(18)PAH; Clar reaction of 7H-benz[de]anthracen-7-one; identification; synthesis; tetrabenzo[a,cd,lm,o]perylene; UV spectrum