Induced Correspondence of a Local π‐Aromatic Sextet in Heteroannulenes: Synthesis and Characterization. Issue 16 (8th March 2016)

• Record Type: Journal Article
• Authors: Mallick, Abhijit; Oh, Juwon; Kim, Dongho; Ishida, Masatoshi; Furuta, Hiroyuki; Rath, Harapriya
• Is Part Of: Chemistry. Volume 22:Issue 16(2016)
• Page Start: 5504
• Page End: 5508
• Publication Date: 2016-03-08
• Subjects: aromaticity -- cross-conjugation -- heteroannulenes -- unconventional pyrrole connectivity -- unorthodox tripyrranes; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201600380
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Acid‐catalyzed [3+3] condensation reactions of two hitherto unknown tripyrrane moieties with pentafluorobenzaldehyde has led to the formation of new generation heteroannulene (4.1.4.1) and mutant heteroannulene (1.1.1.1.1.1). Inclusion of local π‐aromatic sextets, namely the N ‐methyl pyrrole rings through β, β‐linkages and α, β‐linkages, has led to the isolation of first ever heteroannulenes cross‐conjugated at four points and two points respectively within the macrocycles. Abstract : Two and four points cross‐conjugated heteroannulenes! ! Two hitherto unknown tripyrrane moieties undergo acid‐catalyzed [3+3] condensation reactions with pentafluorobenzaldehyde to form a new generation heteroannulene (4.1.4.1) and mutant heteroannulene (1.1.1.1.1.1). Inclusion of local π‐aromatic sextets, namely, the N ‐methyl pyrrole rings through β, β‐linkages and α, β‐linkages, has led to the isolation of the first ever heteroannulenes cross‐conjugated at four and two points, respectively, within the macrocycles.