Hofmann degradation of 5α-cholestan-4α- and 5α-cholestan-4β-yltrimethylammonium salts
Abstract
Alkaline degradation of 5α-cholestan-4α-yltrimethylammonium iodide gives mainly 5α-cholestan-4α-yldimethyl-amine with a little cholest-3-ene, while the 4β-isomer gives cholest-4-ene. The unstable 4β-iodide also readily yields cholest-4-ene in boiling neutral alcohol. The mechanism of these and previously studied degradations with related quaternary salts is discussed.