Tin-heteroatom bonds

Various organotin compounds with tin-heteroatom bonds are synthesized by the reactions of halostannanes with the corresponding heteroatom nucleophiles. For example, trialkyltin alkoxides and trialkyltin amides are prepared by the treatments of halostannanes with sodium alkoxides (eq (139)) [134] and lithium amides (eq (140)) [135], respectively. Tin alkoxides are also formed by the reaction of alcohols with tin amides (eq (141)) [136]. 

Table l6l. Dlorganotln Pseudohalides Containing Tin-Heteroatom Bonds... 

Table 1. Diorganotin Salts or Esters Containing Tin-Heteroatom Bonds R2Sn(0R)X ...

CmGANOTIN OXIDES AND HYDROXIDES CONTAINING TIN-HETEROATOM BONDS... 

All compounds are listed in Table 233 Diorganotin thioacid derivatives containing tin-heteroatom bonds may be found in Subchapters <-.1.6 and... 

The SRN1 process has proven to be a versatile mechanism for replacing a suitable leaving group by a nucleophile at the ipso position. This reaction affords substitution in nonactivated aromatic (ArX) compounds, with an extensive variety of nucleophiles ( u ) derived from carbon, nitrogen, and oxygen to form new C—C bonds, and from tin, phosphorus, arsenic, antimony, sulfur, selenium, and tellurium to afford new C-heteroatom bonds. 

The most relevant results regarding the SRN1 substitutions have been extensively reviewed [1-5] consequently, in this chapter we indude only the most recent and major representative synthetic examples in the aromatic system, relating to C—C and C-heteroatom bond formation with sulfur and tin nudeophiles, and ring-dosure reactions. 

Anions derived from tin, phosphorus, arsenic, antimony, sulfur, selenium, and tellurium are known to react at the heteroatom to form a new carbon-heteroatom bond in good yields. 

Besides carbon-halogen bonds, Bu3SnH is used routinely for hydrogenolysis of various carbon-heteroatom bonds. The deoxygenation from alcohols has been performed by a Barton-McCombie reaction where the addition of tin hydride to the triple bond is suppressed (Equation (2)).29-31... 

Organoselenium compounds are very versatile radical precm-sors which are widely used. Due to their stability and ease of preparation, they offer imique advantages over organic halides as radical precm-sors. They can be utilized in tin mediated radical reactions as weU as in group transfer reactions for the formation of carbon-carbon bonds and carbon-heteroatom bonds. Selenols and diselenides have found applications as reducing agents and radical traps, respectively. A survey of these different reaction types wiU be given. Information about new reactions based on electron and photoelectron transfers wiU also be provided. 

Heteroatomic metal-metal bonds can be formed by a variety of synthetic routes as illustrated below for tin ... 

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