87514-90-7Relevant academic research and scientific papers
109. The Intramolecular Ramberg-Baecklund Reaction: A Convenient Method for the Synthesis of Strained Bridgehead Olefins
Becker, Konrad B.,Labhart, Marco P.
, p. 1090 - 1100 (1983)
The stereochemical aspects of the intramolecular Ramberg-Baecklund reaction, i.e. the 1,3-elimination of hydrogen halide followed by sulfur dioxide extrusion, have been studied on the α-bromosulfones of the 1-thiadecalin series.Whereas the cis,exo-bromosulfone 23a containing the ideal W-type arrangement of the reacting atoms undergoes a clean Ramberg-Baecklund reaction, the trans,exo- and trans,endo-bromosulfones, 24a and 24b, respectively, lead to an α,β-unsaturated sulfone by simple 1,2-elimination of HBr.Application of the Ramberg-Baecklund reaction to 9-bromo-8-thiabicyclodecane-8,8-dioxide (17) permits a short synthesis of the Bredt olefin bicyclonon-1(8)-ene (5), which can be isolated but shows the typical high reactivity of other methylene-bridged (E)-cyclooctenes.
