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5,6,7,8‐Tetramethylenebicyclo[2.2.2]oct‐2‐ene as “Bis(diene)” in Repetitive Diels‐Alder Reactions
Author(s) -
Wegener Stefan,
Müllen Klaus
Publication year - 1991
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.19911240936
Subject(s) - chemistry , diels–alder reaction , diene , ene reaction , bridged compounds , alder , bicyclic molecule , stereochemistry , medicinal chemistry , organic chemistry , botany , catalysis , natural rubber , biology
The synthesis of ladder‐type oligomers by repetitive Diels‐Alder reactions is described. The title compound 1 has been treated with the “bis(dienophile)” 2 at high pressure (7.5 kbar). Under these conditions the formation of oligomers with up to 33 laterally anellated six‐membered rings has been achieved. An attempt has been made to analyze the complex stereochemistry of the cycloadditon by using the model compounds 5a , 5b .