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70eV Spectrum abstraction acetic acid acetone allylic allylically activated Anal analogous angular methyl group aqueous benzoate brine and dried C-3 axial C-3 equatorial C-ll calc carbon atoms carbonium Chem chloride cholest cholest-8 cholestenes cholesterol acetate chromatography crude Deuterated deuterium labeling deuterium transfer diester diglyme double bond dried over MgSO electron impact ester ether extracts ether/hexane extracted into ether Fig0 formation of m/e free sterol gave hexane hydrogen transfer isomer isomerization isotopic composition ketone labeled cholesterols lead tetraacetate loss of C-19 m-iodobenzoate mass spectrometer mass spectrum methanol mixture molecular ion NMR identical olefins oxidation peak at m/e pregnane proton proton transfer reaction recrystallized recrystallized from methanol reduced refluxed result ring D cleavage ring D fragment rinsed rupture saturated steroids Scheme shift side chain silica solution solvent spectra spectrum of cholesterol steroidal olefins sterol stirred substituent Table unlabeled compound vinyl Wyllie