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DOI: 10.1055/s-0030-1260825
Lithium Dibenzylamide, a Simple, Selective and Highly Efficient Catalyst for Isocyanate Cyclotrimerization to Isocyanurate
Publication History
Publication Date:
28 June 2011 (online)
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Abstract
Lithium dibenzylamide catalyzed the rapid and essentially quantitative cyclotrimerization of a variety of isocyanates under mild conditions and could be recycled for six times in high yield.
Key words
lithium amides - catalysis - isocyanates cyclotrimerization - isocyanurates
- Supporting Information for this article is available online:
- Supporting Information
- Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0013th:
- Primary Data
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References and Notes
Representative Procedure: An oven-dried Schlenk tube under nitrogen was charged with phenyl isocyanate, lithium dibenzylamide (0.1 mol%), and Et2O (30 mL). The reaction mixture was stirred at r.t. for 2 min. The resulting precipitate was filtered off, washed with Et2O (3 × 3 mL), and dried under reduced pressure to give the isocyanurate 1,3,5-triphenyl-1,3,5-triazinane-2,4,6-trione (1) as a white solid.
31Procedure for Recycling Experiment of Lithium Dibenzylamide: Phenyl isocyanate was added to a solution of lithium dibenzylamide (0.1 mol%) in Et2O (30 mL) with stirring. The reaction mixture was stirred at r.t. for the allotted time and filtered via a canula filter. The Et2O filtrate was subjected to a second reaction cycle. This procedure was repeated six times (for details see Table [³] ).