Reactions of S-trimethylstannyl and S-(3-trimethylstannylpropyl) derivatives of 1,5-pentanedithiol with N,4-dichlorobenzenesulfonamide sodium salt

Difunctional derivatives of 1,5-pentanedithiol, 1,5-bis(trimethylstannylthi o)pentane (CH2)(5)(SSnR3)(2) and 1,5-bis(3-trimethylstannylpropylthio)penta ne (CH2)(5)[S(CH2)(3)SnR3](2) (R = Me), differ by mutual arrangement of the tin and sulfur atoms and therefore react differently with N,4-dichlorobenz enesulfonamide sodium salt ArSO2N(Na)B (Ar = 4-ClC6H4). The first of these substrates possesses two direct SnS bonds which are cleaved by the action o f 2 equiv of 4-ClC6H4SO2N(Na)Cl (desulfurization). The resulting pentamethy lenedithiobis-sulfonamide (CH2)(5)[SN(SnMe3)SO2Ar](2) undergoes oxidative i mination of both S(II) atoms with additional 2 equiv of 4-ClC6H4SO2N(Na)Cl to afford sulfinimidamide derivative (CH2)(5)[S(=NSO2Ar)-N(SnR3)SO2Ar](2). By contrast, both pairs of the sulfur and tin atoms in the bissulfide (CH2) (5)[S(CH2)(3)SnR3](2) are separated by a trimethylene bridge, and this subs trate reacts with 2 equiv of 4-ClC6H4SO2N(Na)Cl to form tin-containing bis- sulfimide (CH2)(5)[S(=NSO2Ar)(CH2)(3)SnR3](2). According to the H-1 and C-1 3 NMR data, interaction between two pairs of the tin and sulfur atoms at bo th ends of the bis-sulfimide molecule gives rise to independent sterically favorable coordination rings.