Beilstein J. Org. Chem.2014,10, 2550–2555, doi:10.3762/bjoc.10.266
Analytical Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany 10.3762/bjoc.10.266 Abstract An addition/elimination sequence of seleniumhalides 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.
Keywords: acetylenes; dienes; [2.2]paracyclophane; seleniumhalides
][20]. For electrophilic selenium species, most of the investigations have been carried out in order to study the addition mechanism of seleniumhalides to alkenes [21][22][23]. Less work has been reported on the addition of selenyl reagents to alkynes [24][25]. In contrast to the chemistry of sulfur
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Graphical Abstract
Scheme 1:
Reactions of selenium dichloride and selenium dibromide with pseudo-geminal bis(acetylene) 1.