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.
E. N. Wall and J. McKenna, J. Chem. Soc. B, 1970, 318 DOI: 10.1039/J29700000318
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