perchloric acid in dichloromethane 4.25 h; Further byproducts given;

1: 68 percent / hydrazine, conc. H2SO4 / bis-(2-hydroxy-ethyl) ether / 87 h / 170 - 180 °C / caution: one tube exploded in the oven, when reaction was attemted on a larger scale (1.2 g of ketone) 2: 58 percent / pyridine / in the freezer, overnight 3: 80 percent Chromat. / 1) NaOCH3 / multistep reaction: 2) irradiation; separation of the intermediate 13-diazospiro<12.11>tetracosane View Scheme

perchloric acid in dichloromethane 4.25 h; Yield given. Further byproducts given. Title compound not separated from byproducts;

1: 58 percent / pyridine / in the freezer, overnight 2: 80 percent Chromat. / 1) NaOCH3 / multistep reaction: 2) irradiation; separation of the intermediate 13-diazospiro<12.11>tetracosane View Scheme

sodium methylate in diethylene glycol dimethyl ether 1 h; Heating; Yield given;

perchloric acid in hexane 96 h; Ambient temperature; Yield given. Yields of byproduct given;

sodium methylate 1) heptane, room temperature, 2 h, 2) irradiation, 80 min; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

perchloric acid Ambient temperaturevarious dehydration reagents; Product distribution;

sodium hydride 1) heptane, room temperature, 4 h, 2) irradiation, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

trifluoroacetic acid 0.2 h; Ambient temperaturevarious dehydration reagents; Product distribution;