Nitrous acid deamination of cis-1-aminomethyl-4-phenylsulfonyl-1-cyclohexanol gives 60% of epoxide and 23% of ring-expanded ketone whereas the trans isomer gives 28% of epoxide and 60% of ring-expanded ketone. The large proportion of epoxide is accounted for by the inductive effect and the field effect of the phenylsulfonyl group; a conformational effect wherein the CH2NH2 group leads to more epoxide when in an equatorial conformation than in an axial is also observed in this reaction. This study required the preparation of 4-phenylthio and 4-phenylsulfonyl cyclohexanols and cis- and trans-1-methyl cyclohexanols.
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