Synthesis of 1,9-Disubstituted Phenalenes and their Structural Assignment by HMQC and HMBC Experiments

Abstract

The reaction of phenalenone with various sulphur‐derived nucleophiles gave 1‐hydroxy‐9‐alkyl‐ or ‐aryl‐thiophenalenes. The complexity of the aromatic 1H and 13C signals does not allow straightforward assignments. These were rendered possible by the use of two‐dimensional 1H‐detected heteronuclear one‐bond (HMQC) and multiple‐bond (HMBC) correlation techniques.

Fungal phenalenones: chemistry, biology, biosynthesis and phylogeny

“…1 Chemists have also synthesized many phenalenone derivatives bearing signicant biological activity. [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] Phenalenone derivatives have been reported both from higher plants and microbial sources, 18 and possess signicant biological and chemical importance. Despite their importance, this class of natural polyketides did not receive due attention, therefore, to explore these compounds further, we have focused on phenalenone derivatives, especially of fungal origin.…”

Dearomatization of Naphthalene: Novel Stereoselective Cyclization Reactions Promoted by Osmium(II)

“…Nonetheless, product 21 was oxidized in a H 2 O/ether solution with AgOTf to give a hydrocarbon product ( 22 ) in an isolated overall yield of 20% from naphthalene. 1 H and 13 C NMR and DEPT data for 22 closely matched that of the parent phenalene, − with the exception that compound 22 has one less methine group, has a methyl group, and has an additional quaternary carbon. Although spectral data may be consistent with other methylphenalene isomers as well, we have assigned 22 as 9-methylphenalene.…”

The isomers of phenalene and their singlet and triplet states: A Hartree–Fock and density functional computational investigation

“…In these systems, the ligand may bind to a metal in an g 1 -mode [14], in an g 3 -allylic fashion [14][15][16], or in an g 6 -mode [14,17,18]. Computationally, a lithium, calcium, or aluminium atom has been shown to form strong covalent bonds to the phenalenyl moiety [19].…”

“…Computationally, a lithium, calcium, or aluminium atom has been shown to form strong covalent bonds to the phenalenyl moiety [19]. In addition, 1H-phenalene itself and derivatives of (1) have been shown to form organometallic complexes with a variety of metals [17,18]. While a significant amount of information is available for 1H-phenalene and for the phenalenyl cation, neutral radical, and anion, there is a dearth of information concerning the remaining three isomers of phenalene.…”