1: 1.) 100percent HNO3, AcOH, 2.) 30percent aq. AcOH / 1.) 20 deg C, 0.5 h, 2.) reflux, 0.5 h 2: 85 percent / 100percent HNO3, Ac2O / 5 h / 20 °C 3: 75 percent / 60percent aq. AcOH, 60percent aq. HNO3 / 5 h / 85 °C 4: 80 percent / NH2NH2*H2O, Raney-Ni / propan-2-ol / 10 h / Heating View Scheme

2,2'-azo-bisisobutyronitrile T=400°C; 40 h; ΔG(excit.), further study of <4-13C>-, <3,6-D2>-, and <4,4-D2>-labelled homoadamantane; Product distributionMechanismThermodynamic data;

lead(IV) acetate; sodium hydroxide; trifluoroacetic acid; lithium chloride 1.) CH2Cl2, 24 h, dark, 2.) 16 h, reflux; Yield given. Multistep reaction. Yields of byproduct given;

2,2'-azo-bisisobutyronitrile T=400°C; 40 h; ΔG(excit.), further study of <4-13C>-, <3,6-D2>-, and <4,4-D2>-labelled homoadamantane; Product distributionMechanismThermodynamic data;

bromine 2 h; Ambient temperature;

3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane T=65°C; 24 h;