The reaction of BOC2O in the presence and absence of DMAP was examined with some amines, alcohols, diols, amino alcohols, and aminothiols. Often, unusual products were observed depending on the ratio of reagents, reaction time, polarity of solvent, pKa of alcohols, or type of amine (primary or secondary). In reactions of aliphatic alcohols with BOC2O/DMAP, we isolated for the first time carbonic-carbonic anhydride intermediates; this helps explain the formation of symmetrical carbonates in addition to the O-BOC products. In the case of secondary amines, we succeeded to isolate unstable carbamic-carbonic anhydride intermediates that in the presence of DMAP led to the final N-BOC product. The effect of N-methylimidazole in place of DMAP was also examined.

中文翻译：

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再次考察了碳酸二叔丁酯和4-（二甲基氨基）吡啶。他们与胺和醇的反应

用一些胺，醇，二醇，氨基醇和氨基硫醇检查在存在和不存在DMAP的情况下BOC2O的反应。通常，根据试剂的比例，反应时间，溶剂的极性，醇的pKa或胺的类型（伯胺或仲胺）观察到不寻常的产物。在脂族醇与BOC2O / DMAP的反应中，我们首次分离出碳-碳酸酐中间体。这有助于解释除O-BOC产物外还形成对称的碳酸盐。在仲胺的情况下，我们成功地分离出不稳定的氨基甲酸酯-碳酸酐中间体，该中间体在DMAP的存在下会生成最终的N-BOC产物。还检查了N-甲基咪唑代替DMAP的作用。