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- In an attempt to observe silylenamine formation, the solvent was altered to allow for reflux at a higher temperature. Solvent investigated include DCM, THF, benzene, and toluene. To probe the influence of concentration on the silylamination of diethyl acetylenedicarboxylate using 1 the concentrations of the reagents were halved (0.85 M silylamine, 0.71 M alkyne) from the standard conditions described in the general procedure and also doubled (3.4 M silylamine, 2.8 M alkyne); however, no change in the proportion of silylenamine was observed. The time of the reaction was increased from 6 hours to 12 hours, in addition to allowing the reaction to proceed for 1–3 days. No change in the proportion of silylenamine was observed.
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- Hexamethyldisiloxane is the presumed by-product of hydrolysis for Table 1, Entries 1-8, though it is likely removed, along with the solvent, under vacuum.
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