n-butyllithium in tetrahydrofuran; hexane T=0°C; 1.5 h;

1: 79 percent / m-chloroperbenzoic acid, NaHCO3 / CH2Cl2 / 1.) 0 deg C, 3 h, 2.) room temperature, overnight 2: n-Bu3SnH / benzene / Ambient temperature 3: 17 percent / tetrahydrofuran; hexane / 0.08 h / -70 °C / reaction at 0 deg C; electrocyclic ring opening of β-lithiocyclopropyloxirane, generationand trapping of (2Z,4E)-cyclohepta-2,4-dienol View Scheme

1: n-Bu3SnH / benzene / Ambient temperature 2: 17 percent / tetrahydrofuran; hexane / 0.08 h / -70 °C / reaction at 0 deg C; electrocyclic ring opening of β-lithiocyclopropyloxirane, generationand trapping of (2Z,4E)-cyclohepta-2,4-dienol View Scheme

1: 68 percent / t-BuOK / pentane / 4 h / 0 °C 2: 79 percent / m-chloroperbenzoic acid, NaHCO3 / CH2Cl2 / 1.) 0 deg C, 3 h, 2.) room temperature, overnight 3: n-Bu3SnH / benzene / Ambient temperature 4: 17 percent / tetrahydrofuran; hexane / 0.08 h / -70 °C / reaction at 0 deg C; electrocyclic ring opening of β-lithiocyclopropyloxirane, generationand trapping of (2Z,4E)-cyclohepta-2,4-dienol View Scheme

n-butyllithium in tetrahydrofuran; hexane 0.5 h; temperature < -70 deg; Yields of byproduct given. Title compound not separated from byproducts;

in tetrahydrofuran; hexane T=-70°C; 0.0833333 h;

pyridinium chlorochromate in dichloromethane Ambient temperature;