Abstract
The fluoriranium ion (CH2CH2*, la) is shown to exist as an intermediate within ion-neutral complexes derived from the molecular ions of @-fluorophenetole (8). Ion-neutral complexes containing the isomeric ion CH3CHF+ (2a) also occur. The parent neutral 8 favors the gauche conformation, and theoretical calculations show that the radical cation 8'+ and the conjugate acid ions should also favor their gauche conformers. NMR analysis of the neutral fluoroethylenes from deuterated analogues of 8'+ show that fluorine bridging to form la and hydride shift to form 2a take place competitively and not sequentially. Nearly the same ratios of ClH2DF loss to C2HD2F loss are observed for the radical cations and from the MD+ conjugate acid ions. By contrast, free C2H2D2P ions quenched by chloride abstraction from (CH3),CCI have the structure 29, in which sequential transpositions have occurred. The difference between free ions and ions within complexes is ascribed to the millionfold difference in lifetimes under the experimental conditions.
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