Versatile approach to α-alkoxy carbamate synthesis and stimulus-responsive alcohol releaseElectronic supplementary information (ESI) available. See DOI: 10.1039/c2ob26571k

A series of α-alkoxy carbamates that cleave under mild conditions to release alcohols has been synthesized through a multicomponent process. The relationship between structural features in these compounds and the rate of alcohol release in the presence of basic hydrogen peroxide has been studied. The preparation of carbamates that cleave under other conditions has been demonstrated. A structure-reactivity relationship for the stimulus-induced breakdown of α-alkoxy carbamates has been conducted and peroxide-triggered anti-oxidant release was demonstrated.