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Diels–Alder reactions of 3,6-disubstituted 1,2,4,5-tetrazines. Synthesis and X-ray crystal structures of diazafluoranthene derivatives


Rahanyan, N; Linden, A; Baldridge, K K; Siegel, J S (2009). Diels–Alder reactions of 3,6-disubstituted 1,2,4,5-tetrazines. Synthesis and X-ray crystal structures of diazafluoranthene derivatives. Organic & Biomolecular Chemistry, 7(10):2082-2092.

Abstract

The synthesis of a series of 3,6-disubstituted-1,2,4,5-tetrazines has been effected using an inverse electron demand [2 + 4] cycloaddition strategy. The crystal structures of 18 members of this series of diazafluoranthenes are reported. Stereochemical analysis shows that diazafluoranthenes, substituted across the bay region, are helically-twisted strained aromatic molecules. The dihedral angle between pyridazyl vs naphthyl rings ranges from 0.5° to 20.9°, and follows the degree of steric congestion in the bay region. The crystal structures are compared to computational structures determined using density functional theory, with the M06-2X/cc-pVDZ method.

Abstract

The synthesis of a series of 3,6-disubstituted-1,2,4,5-tetrazines has been effected using an inverse electron demand [2 + 4] cycloaddition strategy. The crystal structures of 18 members of this series of diazafluoranthenes are reported. Stereochemical analysis shows that diazafluoranthenes, substituted across the bay region, are helically-twisted strained aromatic molecules. The dihedral angle between pyridazyl vs naphthyl rings ranges from 0.5° to 20.9°, and follows the degree of steric congestion in the bay region. The crystal structures are compared to computational structures determined using density functional theory, with the M06-2X/cc-pVDZ method.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2009
Deposited On:17 Jan 2010 08:53
Last Modified:17 Feb 2018 23:35
Publisher:Royal Society of Chemistry
ISSN:1477-0520
OA Status:Closed
Publisher DOI:https://doi.org/10.1039/b820551e
PubMed ID:19421446

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