Organotin radical anions

Photoassisted electron transfer can be induced between a triaryltin chloride and an electron-rich olefin to give the organotin radical anion and then the neutral stannyl radical (equation 20-17).46... 

Organotin radical anions which have been observed in solid matrices are listed in Table 20-8. 

Supported Ditin Reagents. Ditin reagents can be obtained by reduction of organotin halides with arene metal radical anions or by dehydrogenation of supported organotin hydrides in the presence of Pd(PPh3)4 (Scheme 5.5.13) ... 

As with the silanes, some of the most useful synthetic procedures involve electrophilic attack on alkenyl and allylic stannanes. The stannanes are considerably more reactive than the corresponding silanes because there is more anionic character on carbon in the C—Sn bond and it is a weaker bond.103 104 There are also useful synthetic procedures in which organotin compounds act as carbanion donors in palladium-catalyzed reactions, as discussed in Section 8.2.3 Organotin compounds are also very important in free-radical reactions, which will be discussed in Chapter 10. 

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