ORGANOTIN DERIVATIVES IN THE UMPOLUNG OF 1,3-DITHIAN-2-YLIDES TO 1,3-DITHIAN-2-YLIUM SALTS

Article abstract of DOI:10.1016/0022-328X(86)80130-9

Lithiated 1,3-dithianes react with trialkyltin or triphenyltin chlorides to form the corresponding 1,3-dithian-2-yltin compounds.The dithiane C(2)-Sn bond in the trialkyltin or triphenyltin compounds is selectively cleaved by iodine, with formation of 1,3-dithian-2-ylium triiodides which can be transformed into the corresponding tetrafluoroborate salts.The (1)H and (13)C NMR data are consistent with the salt like structures.The ambident nature of β-styryl derivatives is discussed.Preferential cleavage of the C(2)-Sn bond in the stannyl derivatives is evident in the mass spectra.