Triorganotin Alkoxides

Triorganotin alkoxides are reported from hydrocarbon alcohols and phenols and a large variety of functionally substituted hydroxy compounds. Derivatives listed in Tables 172 through l80 are prepared by methods from the following scheme. 

I Insertion reactions into labile carbon-tin bonds  

IV Reactions with organotin oxides, hydroxides and alkoxides  

R = organic group, may be different in one molecule R = R, may be functionally substituted M = Li, Na, K, MgX X - halogen. Additional references to triorganotin alkoxides may be found in Chapter 8.1. 

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Stannoic acids react with triols, e.g. triethanolamine (equation 91). Triorganotin alkoxides RsSnOR (as well as oximes, etc.), similar to RsSnOH, show a strong tendency... 

Organotin alkoxides and phenoxides can be prepared from the reaction of an alkali metal alkoxide or phenoxide with the appropriate organotin halide. Triorganotin alkoxides and phenoxides are available from the reaction of bis(triorganotin) oxides with alcohols or phenols or the corresponding carbonates, and the amides R Sn(NR"2)4 react with alcohols to give the corresponding alkoxides. 

The sodium halide which is formed in these reactions is very finely divided, and may be difficult to filter off.2 A more convenient way of preparing the triorganotin alkoxides and phenoxides is by the azeotropic dehydration of a mixture of the bis(trialkyltin) oxide and alcohol or phenol in a solvent such as benzene or toluene.4... 

Some typical triorganotin alkoxides and phenoxides are listed in Table 14-1. 

Exchange reactions also occur readily between alkoxyl groups and other electronegative groups bonded to tin. Triorganotin alkoxides, which are difficult to prepare by other methods, can often be made by exchange between a tin halide and an appropriate tin alkoxide.38... 

The use of 0-metallation of alcohols or enols to enhance their reactivity towards electrophiles, such as aldehydes or alkyl or acyl halides has been reported by Davies.The reaction of triorganotin alkoxides with other polar multiply-bonded acceptors was also reported (Scheme 6.3.8). 

Scheme 6.3.8 The reaction of triorganotin alkoxides with polar multiply bonded acceptors...

Mossbauer and Sn NMR spectroscopic studies of several diorganotin alk-oxides, R2Sn(OR )2, and triorganotin alkoxides, R3SnOR, indicate self-assembly... 

Listing of unsubstituted triorganotin alkoxides concludes in Table 172. 

TRIORGANOTIN ALKOXIDES DERIVED FROM UNSATURATED ALCOHOLS... 

Table 175. Triorganotin Alkoxides Derived from Heterocyclic Alcohols RsSnOR ... 

The compounds are listed in Table 173 Additional triorganotin alkoxides derived from substituted alcohols may be found in Tables 175 177 179 nd 180. 

TRIORGANOTIN ALKOXIDES DERIVED FROM ALCOHOLS CONTAINING OXYGEN FUNCTIONS... 

Triorganotin alkoxides with nitrogen or phosphorus containing alcohols are listed in Table 177 Additional substituted derivatives may be found in Subsections 3 3 1 3 3 3 1 6.2 and Tables I76 and I80. 

Table 175 Triorganotin Alkoxides Derived from Halogen Substituted Alcohols... 

Table 177 Triorganotin Alkoxides Derived from Alcohols Containing Nitrogen and Phosphorus R3SnOR ...

Additional substituted triorganotin alkoxides containing metallic substituents are listed in Subchapters 2A.3> 2-5 3 and 2.7.1.2. 

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