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4FormationoftheCarbon–TinBond1,2

Theprincipalmethodsforformingthecarbon-tinbondinvolvethereactionoforgano-

metallicreagentswithtincompounds(equation4-1),thereactionofstannylmetallic

compoundswithorganichalides(equation4-2),thereactionoftinortin(II)compounds

withalkylhalides(equation4-3),thehydrostannationofalkenesoralkynes(equation

4-4),thereactionofacidichydrocarbonswithSn–OandSn–Nbondedcompounds

(equation4-5),andcarbonyl-formingeliminations(equation4-6);thesymbolsnre-

presents¼Sn.

RM+snXsnR+MX(4-1)

snM+RXsnR+MX(4-2)

SnorSnX+RXRSnXorRSnX(4-3)

2223

snH+C=CorCCsnC-CHorsnC=CH(4-4)

Rδ−Hδ++snOorsnNsnR(4-5)

RSnOCRRSnR+O=C(4-6)

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4.1ReactionofOrganometallicReagents

withTinCompounds

Thenucleophilicalkylationofatincompoundwithanorganometallicreagentisthe

mostcommonroutetoorganotincompounds.

4-nRM+RSnXRSnR+4-nMX(4-7)

n4-nn4-n

ThemetalMiscommonlymagnesiuminaGrignardreagent,orlithium,oralumin-

ium,andXiscommonlyhalide.Selectivepartialalkylationofthetinisusuallydifficult

toachieve,andthereactionistakentocompletiontogiveR4Sn(equation4-8);ifany

organotinhalidesarep