hydrogen; palladium on activated charcoal in methanol P=760 Torr; 17 h; Ambient temperature;

1: 1) NaH, HMPA / 1) THF, mineral oil, r.t., 1 h, 2) reflux, 12 h 2: 96 percent / H2 / 10percent Pd-C / methanol / 17 h / 760 Torr / Ambient temperature View Scheme

1: NaI / acetone / 17 h / Heating 2: 12 percent / Bu3SnH, AIBN / benzene / 18 h / Heating; other time; other cyclic keto-compounds; three-carbon ring expansion to large rings View Scheme

1: 85 percent / NaH / benzene; paraffin / 1 h / Heating 2: 1) NaH, HMPA / 1) THF, mineral oil, r.t., 1 h, 2) reflux, 12 h 3: 96 percent / H2 / 10percent Pd-C / methanol / 17 h / 760 Torr / Ambient temperature View Scheme