Tin for organic synthesis. Part 15 : The use of 1,2-bis(trimethylstannyl) -1-alkenes in electrophilic destannylation reactions

Article abstract of DOI:10.1016/S0022-328X(96)06151-7

Z-1,2-Bis(trimethylstannyl)-1-alkenes show different types of reaction behaviour towards various electrophiles. p-Tolysulphonyliso-cyanate forms five-membered tin-nitrogen-containing heterocycles. 1,1-Dichloromethylmethyl ether reacts with carbofunctionalised distannylalkenes to yield α,β-unsaturated aldehydes, which are useful tools for the synthesis of further substituted vinylstannanes. Z-1,2-Bis(trimethylstannyl)- 1-alkenes containing heteroatoms such as O or N undergo only protodestannylation with this electrophile. The reaction of Z-1,2-bis (trimethylstannyl)-1-alkenes with trimethylsilyl chlorosulphonate followed by hydrolysis with aqueous NaHCO₃ provides the corresponding sodium sulphonates. SO₂ and SO₃ undergo insertion into both tin-carbon bonds in an ipso- and stereospecific manner to form bis-sulphinic- or bis-sulphonic bis(trialkylstannyl) esters.