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Synthesis of a Bisdienophilic Phthalocyanine and of Precursors for Repetitive Diels‐Alder Reactions Based on Hemiporphyrazines and Phthalocyanines
Author(s) -
Stihler Patrick,
Hauschel Bernd,
Hanack Michael
Publication year - 1997
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19971300620
Subject(s) - chemistry , isoindoline , phthalocyanine , diels–alder reaction , condensation , organic chemistry , catalysis , physics , thermodynamics
The specific synthesis of a metal‐free bisdienophilic phthalocyanine 193 , suitable for repetitive Diels‐Alder reactions, is reported. This was achieved by condensation of 191 ,3,3‐trichloro‐6/7‐nitroioindolenine ( 191 ) and 4,9‐dibutoxy‐2,3,5,8‐tetrahydro‐1,3‐diimino‐1 H ‐5,8‐epoxybenz[ f] isoindoline ( 2 ). The ability of 3 to undergo Diels‐Alder reactions was tested by reaction with an excess of 1,2,3,4‐tetraphenylcyclopentadienone ( 5 ). Experimental data of the hemiporphyrazines 9, 10 , and 11 , which can be used as precursors for the synthesis of ladder polymers, are also given in the Experimental Section.