Abstract
AbstractBoth H2O and HDO are eliminated from protonated d11‐cyclohexanol under chemical ionization conditions using methane as the reagent gas. The elimination of H2O and HDO from the [M+H]+ ions of cyclohexanol specifically labeled with deuterium in the 1; 2,6; 3,5; and 4 positions has been measured. It is found that there is considerable selectivity as to the position from which deuterium is lost in the elimination of HDO. That is, transfer from C‐4 is favored, some transfer from C‐3(5) occurs, little deuterium is lost from C‐2(6) and none is lost from C‐1. A mechanism involving ring protonation and ring opening followed by deuterium transfer to oxygen with subsequent loss of HDO is proposed to account for these observations.
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