The electrophilic cleavage of cyclopropylcarbinylstannanes. Confirmation of Traylor's prediction

Article abstract of DOI:10.1016/S0040-4039(00)74893-3

The reaction of cyclopropylcarbinyltrialkylstannanes (CPCSnR₃) 1a (R = Me) and 1b (R = Bu) with sulfur dioxide in chloroform or methanol yields the homoallylic tin sulphinates 2a and 2b respectively. The reaction of 1a with iodine in chloroform yields predominantly 4-iodo-1-butene (3) and trimethyltin iodide while in methanol the corresponding reaction yields CPCSnMe₂I (4) and methyl iodide.