Condensed Cyclobutane Aromatic Compounds. XXIV. The Mechanism of Thermal Rearrangement of the Linear Benzocyclobutadiene Dimer: Synthesis of 9,10-Benzocyclobutenoanthracene | 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

8511653

Reference Type

Journal Article

Title

Condensed Cyclobutane Aromatic Compounds. XXIV. The Mechanism of Thermal Rearrangement of the Linear Benzocyclobutadiene Dimer: Synthesis of 9,10-Benzocyclobutenoanthracene

Author(s)

Cava, MP; Pohlke, R

Year

1963

Is Peer Reviewed?

Yes

Journal

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904

Volume

Issue

Page Numbers

1012-1014

Language

English

DOI

10.1021/jo01039a033

Abstract

The thermal isomerization of the linear benzocyclobutadiene dimer to 1,2,5,6-dibenzocycloÃ¶ctatetraene proceeds via a two-stage process. The initial o-quinodimethane type intermediate has been intercepted in the form of adducts with several dienophiles. The p-benzoquinone adduct has been transformed into a hydrocarbon which is identical with the direct adduct of anthracene with benzocyclobutadiene. Â© 1963, American Chemical Society. All rights reserved.