7-Silyl- and 7-silylmethylcycloheptatrienes react with acylnitroso reagents at room temperature to provide the corresponding silyl- and silymethylnorcaradiene cycloadducts. Depending on the reaction conditions, 7-silylmethylcycloheptatriene was also shown to provide, through cascade processes, functionalized cyclohexa-1,3-dienes or bicyclic synthons, incorporating one and two amino groups, respectively, that may be elaborated further, for instance, into sugar mimics.