Diels–Alder Additions to 2, 2'‐Biaceanthrylene. Issue 2 (5th January 2023)

• Record Type: Journal Article
• Authors: Du, Yachu; Pandey, Krishna; Plunkett, Kyle N.
• Is Part Of: Helvetica chimica acta. Volume 106:Issue 2(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-01-05
• Subjects: aromatic compounds -- cyclopenta-fused polycyclic aromatic hydrocarbons -- Diels–Alder reactions -- electrocyclic reactions -- polycycles; Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.202200126
• Languages: English
• ISSNs: 0018-019X

Abstract

Abstract: A series of Diels–Alder reactions between the diene 2, 2'‐biaceanthrylene and several dienophiles is presented. The diene is a cyclopenta‐fused polycyclic aromatic hydrocarbon with anthracene units linked by two cyclopentene rings. Depending on the dienophile, the major product was the result of a single addition (dimethyl acetylenedicarboxylate) or double addition (quinone, benzyne) to the diene. Single crystal X‐ray analysis of the quinone‐derivative shows a propeller‐like structure composed of mixed enantiomers. The synthesis and photophysical properties of these compounds are presented. Abstract :