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- W2065130960 abstract "The stereochemical aspects of the intramolecular Ramberg-Bäcklund 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-thiadecalin1 Throughout this paper ‘1-thiadecalin’ will be used in place of ‘decahydro-1-thianaphthalene’. series. Whereas the cis,exo-bromosulfone 23a containing the ideal W-type arrangement of the reacting atoms undergoes a clean Ramberg-Bäcklund 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-Bäcklund reaction to 9-bromo-8-thiabicyclo[5.2.1]decane-8,8-dioxide (17) permits a short synthesis of the Bredt olefin bicyclo[5.1.1]non-1(8)-ene (5), which can be isolated but shows the typical high reactivity of other methylene-bridged (E)-cyclooctenes." @default.
- W2065130960 created "2016-06-24" @default.
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- W2065130960 date "1983-06-15" @default.
- W2065130960 modified "2023-10-03" @default.
- W2065130960 title "The Intramolecular<i>Ramberg</i>-<i>Bäcklund</i>Reaction: A Convenient Method for the Synthesis of Strained Bridgehead Olefins" @default.
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- W2065130960 doi "https://doi.org/10.1002/hlca.19830660412" @default.
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