H. Detert et H. Meier, CHEMICAL AND SPECTROSCOPICAL PROPERTIES OF MEDIUM-SIZED TRANS-BICYCLO[N.1.0]ALK-2-YNES AND CIS-BICYCLO[N.1.0]ALK-2-YNES, Liebigs Annalen, (7), 1997, pp. 1565-1570
Chemical and spectroscopical properties of cis- and trans- cyclopropan
o-anellated cycloalkynes of medium ring size are investigated and comp
ared with results from force field calculations. IR and C-13-NMR data
of the alkynes reflect the deformation of the triple bond due to ring
strain. Parallel to bending the reactivity increases with decreasing r
ing size, the trans fused alkynes prove to be nearly as reactive as th
e cis fused with a two carbon smaller ring size. The bicycloalkynes ar
e complexed with silver triflate. C-13 NMR reveals that the triple bon
d as well as the cyclopropane serve as ligands.