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Triphenylphosphane 1, its oxide 2 and sulfide 3 undergo one-electron reduction at a mercury cathode in DMF to yield the corresponding radical anions. ESE analysis of the paramagnetic species is facilitated by deuteration and suggests a pyramidal geometry of the radicals. Reduction with potassium metal in DME at low temperature yields also radical anions for 2 and 3. The phosphane 1, however, reacts under phenyl cleavage and potassiumphenyl-assisted ring closure to the dianion of 5H-dibenzophosphole 4. This radical 4 · ⊖⊖  is also obtainod by alkali metal reduction of P-phenyldibenzophosphole o, and its spin distribution is compared to iso-.-π-electronic radicals containing CH, N, O, S, or Se links instead of the phosphorus atom.

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Die Reduktion von Triphenylphosphan-Derivaten zu ihren Radikalanionen und zum Dibenzophosphol-Radikaldianion [1] / The Reduction of Triphenylphosphane Derivatives to their Radical Anions and to the Radical Dianion of Dibenzophosphole [1]