were synthesized and their behaviour in super basic systems MNH(CH,),NH,/H,N(CH,),NH, (M = Li, Na, K) was studied. Instead of the expected products-alcohols with a terminal triple bond-corresponding alkynes as products of the retro-Favorskii type defragmentation reaction was detected.Using the most effective superbase KNH(CH,)NH,/H,N(CH,),NH, the -CH,OH fragment was removed and the corresponding terminal alkynes with a yield of 83-95% were prepared. (E)-2-octadecen-13-yn-1-ol gave under the same conditions a very complicated mixture of compounds.
Anionotropic isomerization of the enynic block of (Z,E)-2-octen-4-yn-1-ol in super basic media MNH(CH,),NH,/H,N(CH,),NH, (M = Li, Na) and the following alkylation in situ of the metallated product was studied. The influence of the strength of the super base and the structure of the alkylating agent to the yield and isomeric composition of products were determined.
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