Summary
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1.
Steric control of the Wittig reaction can be effected by changing the reaction conditions and the structures of the starting compounds.
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2.
Stereoselective synthesis of cis olefins from alkylideneor benzylidene-triphenylphosphoranes and aldehydes can be effected in presence of Lewis bases. The maximum relative yield of cis olefins is attained by carrying out the reaction in N,N-dimethylformamide in presence of Br− and I−, which form complexes with phosphoranes.
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3.
The stereoselective synthesis of trans olefins was effected when the phosphorylid molecule contained an electron-accepting substituent on the ylid C atom. Thus, irrespective of the external conditions, the reaction ofα-(triphenylphosphoranylidene)alkanoic esters with aldehydes gives only the corresponding trans olefins.
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Bergel'son, L.D., Vaver, V.A., Barsukov, L.I. et al. Stereochemistry and mechanism of the wittig reaction. Russ Chem Bull 12, 957–966 (1963). https://doi.org/10.1007/BF00845473
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DOI: https://doi.org/10.1007/BF00845473