Efficient Preparation of the .alpha.,.alpha.,.beta.,.beta.-Atropoisomer of meso-Tetrakis(o-aminophenyl)porphyrin

Chiral "basket handle" binaphthyl porphyrins: synthesis, catalytic epoxidation and NMR conformational studies

“…The statistical mixture of the four atropoisomers αβαβ, ααββ, αααβ and αααα-o-TAPPH 2 was separated by silica gel chromatography column in the ratio 12.5, 25, 50 and 12.5%. The abundance of the four atropoisomers can be changed by thermal treatment of the corresponding nitrophenyl atropoisomers or their Zn derivatives to yield as the major atropoisomer the αβαβ [20] or the ααββ one, respectively [21]. We also prepared the binaphthyl diacid chlorides BN n [12,22], n represents the number of carbons between the binaphthyl residue starting from the (R)-(+)-1,1′-Bi-2-naphthol.…”

Synthesis of the first superstructured chiral corrole

“…Previously, we described the preparation of binaphthyl-strapped porphyrins 12 by condensing the binaphthyl bis(acid chloride) 6a 13 and the α 2 β 2 atropisomer of tetrakis(2-aminophenyl)porphyrin. 14 Unfortunately, a CPK model revealed that the latter strap is too short for the optimized synthesis of a binaphthylcorrole. Thus, we developed a preparation of a new "homologated" binaphthyl bis(acid chloride) 6b the synthesis of which will not be described in this communication.…”

Design, synthesis, structural analysis and atropoisomerisation studies of polynucleating ligands based on porphyrins bearing catechol unitsDedicated to H. B. Kagan on the occasion of his 71st birthday.

“…13 In a similar fashion, the preparation of 4 a2b2 as its Zn complex has been described. 14 Different atropoisomers of 3 were prepared according to the literature. In the case of 3 abab , since to the best of our knowledge no structural data is available, its solid state structure was also investigated by X-ray diffraction on a single crystal (see structural analysis below).…”