Elsevier, Tetrahedron Letters, 8(45), p. 1647-1650
DOI: 10.1016/j.tetlet.2003.12.121
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Reaction of 2,3,7,8,12,13,17,18-octaethylporphyrin with LiR reagents containing functional groups readily yields meso substituted derivatives suitable for further transformations with residues such as –p-C6H5Br, –p-C6H5–CCH, –p-C6H5–NH2 or –(CH2)3–CHCH2. Similar reactions of tetrabenzoporphyrin with alkyllithium reagents afforded the first entry into meso mono- and dialkylsubstituted tetrabenzoporphyrins while reaction of bicyclo[2.2.2]oct-type masked isoindole precursors with LiR followed by in situ retro-Diels–Alder reaction also afforded the 5-phenyl and 5,10-diphenyltetrabenzoporphyrins in high purity.