Some reactions of hexafluorobutyne-2 with phosphines and amines

Abstract
The addition reaction R2EX + CF3C≡CCF3 → R2EC(CF3)=C(CF3)X has been investigated further (E = P and N); 1:1 adducts have been obtained from (C2H5)2PH, (CF3)2PH, (C6H5)2P—P(C6H5)2, and (CH3)2NCl, but not from (CH3)2PCl or (CH3)2P—P(CH3)2. (CF3)2PH also gives a 2:1 adduct. Triphenylphosphine causes the butyne to polymerize at − 78°. A similar but slower reaction takes place with trimethylamine. In the presence of water, trimethylamine and the butyne give the bis(butenyl) ether cis,trans (CF3CH=CCF3)2O as the major product.

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