Toxicity, alkyltin compounds

This method avoids the need for handling toxic alkyltin compounds and the need to isolate and purify sensitive ft -side chain intermediates. It therefore provides a viable method for practical large-scale synthesis of prostaglandins (Scheme 9.18)... 

Because of its high acute toxicity, trimethyltin chloride should be handled using the "basic prudent practices" of Chapter 5.C, supplemented by additional precautions for work with compounds of high acute toxicity (Chapter 5.D). Other alkyltin compounds should be handled using the "basic prudent practices" of Chapter 5.C. 

In addition to all the good features of the Stille couplings, there are a few problems with the use of RSnMles or RSn(n-Bu)3 in aqueous solutions. These compounds are rather volatile and water-insoluble but this can be overcome with the aid of co-solvents. However, the products of the reaction still contain alkyltin species which are toxic and environmentally unacceptable. Furthermore, only one of the four Sn-C units take active part in the... 

The most toxic of the organotin compounds are the trialkyltins, followed by the dialkyltins and monoalkyltins. The tetraalkyltins are metabolized to their tri-alkyltin homologs their effects are those of the trialkyltins, with severity of effects dependent on the rate of metabolic conversion, hr each major organotin group, the ethyl derivative is the most toxic. ... 

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