B. Franck et G. Krautstrunk, NOVEL PORPHYRINOIDS .13. SYNTHESIS AND ELECTROPHILIC SUBSTITUTION OF NEW PARTIALLY BETA-UNSUBSTITUTED [18]PORPHYRINS, Liebigs Annalen der Chemie, (10), 1993, pp. 1069-1073
Three porphyrins 2, 3, and 4, related to Hans Fischer's octaethylporph
yrin 1, but with unsubstituted pyrrole beta-positions were synthesized
via the biladiene pathway. The ring-closing reaction to form the porp
hyrin reveals a conformational control, called helical effect. These n
ew porphyrins made possible an investigation of the regioselectivity o
f electrophilic aromatic substitutions at the porphyrin perimeter.