Steroidal sulphur compounds. Part VII. Pyrolysis and chiroptical properties of 3-alkylsulphinyl-5α-cholestanes

Abstract

Regioselectivity of olefin formation depends on chirality at sulphur in the pyrolysis of 3α-t-butylsulphinyl-5α-cholestanes, but not for the corresponding 3α-butyl sulphoxides. The relevant transition states probably have little double-bond character. Chirality at sulphur is the dominant factor in determining the chiroptical properties of the sulphoxides. The non-olefinic products of pyrolysis of 3α-alkylsulphinyl-5α-cholestanes were investigated.