Three cinnamyl ether spacers (non-methyl, α-methyl, and γ-methyl) for caging of phenols have been synthesized and are physiologically stable. When triggered, the γ-methyl spacer releases phenols (pK 7.8 and 9.8) with a t < 30 s and <2 min in aqueous and aqueous-organic solvent, respectively. The α-methyl spacer releases a phenol (pK 7.8) with a t = 27 and 54 min. For the γ-methyl spacer, the results suggest the presence of a resonance and inductively stabilized aza-cinnamyl methide.
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