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The Cycloaddition‐Cycloelimination Pathway to Homotropilidenes − Synthesis and Properties of Homotropilidenes
Author(s) -
Sauer Jürgen,
Bäuerlein Peter,
Ebenbeck Wolfgang,
DyllickBrenzinger Rainer,
Gousetis Charalampos,
Sichert Heinz,
Troll Theodor,
Wallfahrer Uwe
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200107)2001:14<2639::aid-ejoc2639>3.0.co;2-0
Subject(s) - chemistry , cycloaddition , bicyclic molecule , photodissociation , stereochemistry , medicinal chemistry , photochemistry , organic chemistry , catalysis
The cycloaddition‐cycloelimination reaction sequence between 3,6‐disubstituted 1,2,4,5‐tetrazines 9 and various cyclopropenes 10 provides 3,4‐diazanorcaradienes 11 , which undergo [4+2] cycloadditions with additional cyclopropenes 10 to form tetracyclic azo compounds 12 . Photolysis of these compounds, with accompanying loss of nitrogen, affords homotropilidenes (bicyclo[5.1.0]octa‐2,5‐dienes) 13−26 . Substituents at various positions of the homotropilidene skeleton have been observed to exert significant influences on the Cope rearrangement rate and, in cases of unsymmetrically substituted homotropilidenes, on the equilibrium positions.