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Oxidative Addition of Diorgano Disulfides to Distannyne [{2,6‐(Me 2 NCH 2 ) 2 C 6 H 3 }Sn] 2
Author(s) -
Bouška Marek,
Novák Miroslav,
Dostál Libor,
Růžička Aleš,
Mikysek Tomáš,
Metelka Radovan,
Jambor Roman
Publication year - 2014
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201300907
Subject(s) - chemistry , thio , medicinal chemistry , oxidizing agent , tin , reactivity (psychology) , redox , stereochemistry , organic chemistry , medicine , alternative medicine , pathology
Reactivity of [{2,6‐(Me 2 NCH 2 ) 2 C 6 H 3 }Sn] 2 ( 1 ) towards functionalized diorganodisulfides R 2 S 2 as oxidizing agents was studied. The reactions provided organotin(II) thio derivatives {2,6‐(Me 2 NCH 2 ) 2 C 6 H 3 }Sn(S 2 CNMe 2 ) ( 2 ), {2,6‐(Me 2 NCH 2 ) 2 C 6 H 3 }Sn (SC 6 H 4 ‐2‐NH 2 ) ( 3 ) and {2,6‐(Me 2 NCH 2 ) 2 C 6 H 3 }Sn(SC 5 H 4 N) ( 4 ). The 119 Sn NMR spectroscopic data of 2 – 4 suggest different electronic saturation of the tin(II) atoms in 2 – 4 , which caused redox stability of 2 and easy oxidation of 3 and 4 . The treatment of the latter compounds with diorgano disulfides R 2 S 2 yielded organotin(IV) thio derivatives {2,6‐(Me 2 NCH 2 ) 2 C 6 H 3 }Sn(SC 6 H 4 ‐2‐NH 2 ) 3 ( 5 ) and {2,6‐(Me 2 NCH 2 ) 2 C 6 H 3 }Sn(SC 5 H 4 N) 3 ( 6 ). In addition, oxidation of 3 and 4 with the radical TEMPO (2,2,6,6‐tetramethylpiperidin‐1‐oxyl) provided organotin(IV) hydroxide [{2,6‐(Me 2 NCH 2 ) 2 C 6 H 3 }Sn(SC 6 H 4 ‐2‐NH)(μ‐OH)] 2 ( 7 ) and organotin(IV) oxide [{2,6‐(Me 2 NCH 2 ) 2 C 6 H 3 }Sn(SC 5 H 4 N)(μ‐O)] 3 ( 8 ). All prepared compounds 2 – 8 were characterized by using multinuclear NMR spectroscopy, and the molecular structures of 2 , 4 , 7 and 8 were determined by using X‐ray diffraction. Compounds 2 – 4 were also characterized by cyclic voltammetry.