Bis(trichloromethyl) Carbonate in Organic Synthesis

Although more than a century old compound, only in the last decade has the versatility of bis(trichloromethyl) carbonate (BTC) been demonstrated by numerous examples of its application in the synthesis of some important classes of organic compounds: chlorocarbonyl derivatives, isocyanates, N,N'-disubstituted (poly)ureas, (poly)carbonates, alkyl and acyl chlorides, acid anhydrides, heterocyclic compounds. BTC is fast becoming a useful auxiliary to prepare intermediates for the synthesis of many specific organic compounds, since it reacts with many nucleophiles usually found in organic transformations. Reactions with BTC are normally carried out under mild conditions and oft afford good to excellent yields. Well-defined protocols and procedures, which allow efficient synthesis of a variety of described classes of organic compounds on a large scale, are now available, illustrating the synthetic and technological potential of BTC. Safe handling of solid BTC has been demonstrated, underlying the advantages over its gaseous cogener phosgene. The goal of this review is to present applications of BTC in order to promote the chemistry of this very interesting carbonic acid derivative. It is the authors' belief that the chemistry of BTC will continue to grow and be used extensively by organic chemists and engineers in both new developments and in improving old processes.