Further reactions of secondary amines and arsines with fluorocycloolefins

The generality of the reaction [Formula: see text] has been investigated, and examples are given when M = N, X = F or Cl, Y = F, Cl, H, or As(CH3)2, and n = 1, 2, or 3; and when M = As, X = F or Cl, Y = F, Cl, H, or C2H5, and n = 1 or 2. When M = N, Y = OCH3, and X = Cl, the butenone [Formula: see text] is obtained; the corresponding reaction with (CH3)2AsH gives only a trace of a butenone. When M = N, Y = C2H5, X = Cl, and n = 1, the simple product is not obtained. The nuclear magnetic resonance spectra of the compounds [Formula: see text] (Y = H or F) show similar features, notably a shift to high field of the Y resonance when Z is a dialkylamino group.