Naphthalene → Naphthalene potassium

Participants

Reaction Steps

An H-shaped apparatus, described above, with the vertical arms separated by a horizontal filter tube, was loaded on one side with 1.2 g (Ph3P)3RhH (1.25 mmole) and on the other side, with 49 mg of potassium metal (1.25 mmoles) and 190 mg naphthalene (1.5 mmoles). Very pure tetrahydrofuran (20 ml) was distilled into each side of the H-tube, and the K/C10H8 mixture stirred until dissolution of the K metal to yield green potassium naphthalene was complete. The reddish solution of (Ph3P)3RhH was cooled to -111° C. and the solution of K+C10H8 in THF, was added to it dropwise, with stirring over about 2 hours. When the addition was complete, the solution was stirred at -111° C. for 1 hour, then at -80° C. for 8 hours, and then slowly allowed to warm to room temperature. There resulted a deep brown solution, which was evaporated to total dryness. This residue was extracted with tetrahydrofuran to yield a brown, air-sensitive powder (600 mg). Analyses for all the elements (including K) was in rough agreement with the structural formula: (Ph3P)3RhH-K+. However, the exact structure of the molecule may be more complex.

Provenance & Evidence