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2005
Organo-tin compounds
S 4800
Thiostannylation of Arynes with Stannyl Sulfides: Synthesis and Reaction of
— Arynes, generated in situ from (I) and a fluoride ion,
05- 169 2-(Arylthio)arylstannanes.
are able to insert into the sulfur—tin bond of stannyl sulfides (II) to afford the title stannanes (III), whose carbon—tin bonds are appropriate to transformations into compounds like (V), (VI), and (VII). In most cases of thiostannylation of unsymmetrical
arenes (VIII), almost equal amounts of regioisomeric products (IX) and (X) are obtained, indicating that the reaction proceeds through an aryne intermediate. In contrast,
a phenyl group in 3-substituted arenes such as (XIb) controlls the regioselectivity perfectly to offer (XIIb) as the sole product. — (YOSHIDA*, H.; TERAYAMA, T.;
OHSHITA, J.; KUNAI, A.; Chem. Commun. (Cambridge) 2004, 17, 1980-1981;
Dep. Appl. Chem., Fac. Eng., Hiroshima Univ., Higashi-Hiroshima 739, Japan; Eng.)
— H. Hoennerscheid
2005
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