TIN FOR ORGANIC-SYNTHESIS .12. SYNTHESIS OF AROMATIC AND OLEFINIC SODIUM SULFONATES BY ELECTROPHILIC DESTANNYLATION WITH TRIMETHYLSILYL CHLOROSULFONATE

A mild and effective method for the preparation of a variety of aromat ic, olefinic, and acetylenic sodium sulfonates is described. The react ion of trialkylaryl- (2a-k) and -heteroarylstannanes (4a-d), bis-(1-al kenyl)dibutylstannanes (6a-f), or trialkylalkynylstannanes with trimet hylsilyl chlorosulfonate (1) followed by hydrolysis with aqueous NaHCO 3 provides the sodium sulfonates in an ipso-specific and in the case o f vinylic stannanes stereospecific manner. A comparison of the reactiv ity of stannylated and silylated olefinic compounds 13 and 14 underlin es the greater leaving ability of the stannyl moiety. The in situ prep aration of the stannanes makes it possible to apply the synthetic meth od to natural products such as N-substituted apocodeine (17).