Selenium halide-induced bridge formation in [2.2]paracyclophanes.
An addition/elimination sequence of selenium halides to pseudo-geminally bis(acetylene) substituted [2.2]paracyclophanes leads to new bridges with an endo-exo-diene substructure. The reactions have been found to be sensitive to the substitution of the ethynyl group. The formation of dienes with a zig-zag configuration is related to that observed for non-conjugated cyclic diynes of medium ring size.
Department of Chemistry,"Al. I. Cuza" University of Iasi, 11 Carol I Bv., RO-700506 Iasi, Romania.
Laura G
LG
Sarbu
Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
Henning
H
Hopf
Institute of Inorganic and Analytical Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
Peter G
PG
Jones
Department of Chemistry,"Al. I. Cuza" University of Iasi, 11 Carol I Bv., RO-700506 Iasi, Romania ; Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
Lucian M
LM
Birsa
[2.2]paracyclophane; acetylenes; dienes; selenium halides