193-85-1Relevant articles and documents
Dicyclopentaheptalene (Azupyrene) Chemistry. Jutz Synthesis Byproducts. Synthesis and Thermal Isomerization of 1-Methylazupyrene
Anderson, Arthur G.,Daugs, Edward D.,Kao, L. Glenn,Wang, Jean-Fang
, p. 2961 - 2965 (1986)
The Jutz synthesis of azupyrene (4) has been found to form chloro-, methyl-, and dimethylazupyrene byproducts in the final step.Perchlorate and methoxide ions were shown to cause the chlorination and methylation, respectively.Temperature control at 200-205 deg C reduced the chlorination and the use of ethoxide virtually eliminated the alkylation. 1-Methylazupyrene (7) was synthesized.The termal isomerization of 7 to methylpyrenes was carried out and the products were found to be those predicted by certain of the mechanisms proposed for the azulene to naphthalene isomerization.
REDUCTIVE TRANSFORMATIONS 2. CIS- AND TRANS-1,2-ADDITION OF ELECTROPHILES TO DIANIONIC ?-SYSTEMS
Huber, W.,Irmen, W.,Lex, J.,Muellen, K.
, p. 3889 - 3892 (2007/10/02)
The dianion salt of a polycyclic ?-system is selectively alkylated to yield annulenes with trans- or cis-configuration of the bridging group.The products are suitable models for spectroscopic and structural considerations.