Neither 1-chloronaphthalene nor 2-chloroquinoline reacted with PhzP ions in liquid ammonia. However, in the presence of sodium amalgam [Na (Hg)], reaction did occur, and the substitution products l-naphthyldiphenylphosphine and 2quinolyldiphenylphosphine (isolated as the P-oxides), respectively, were obtained in good yield. p-Bromoanisole reacted with Na (Hg) amalgam in the presence of PhzP ions in liquid ammonia to give ...