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1,5,7‐Triazabicyclo[4.4.0]dec‐5‐en als Reaktionsmedium: Präparativ ergiebige einstufige Herstellung von Etioporphyrin aus Protoporphyrin
Author(s) -
Kämpfen Ulrich,
Eschenmoser Albert
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720202
Subject(s) - chemistry , ene reaction , yield (engineering) , protoporphyrin ix , nuclear chemistry , organic chemistry , metallurgy , photodynamic therapy , materials science
1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene as Reaction Medium: An Efficient One‐Step Formation of Etioporphyrine from Protoporphyrine Heating the commercially available protoporphyrine ( 4 ) in molten 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD) at 200° for 4 h under exclusion of O 2 produces etioporphyrine ( 6 ) in 60–70% yield by bisdecarboxylation and concomitant reduction of the two vinyl groups. Mesoporphyrine ( 5 ) is bisdecarboxylated to 6 in over 80% yield under these conditions in TBD as well as in DBU as the reaction medium.