Abstract
Reactions of hexamethyldisilathiane (HMDST) with carbonyl compounds under the catalytic
activity of CoCl2·6H2O or trimethylsilyltriflate lead to a simple and general access to thioaldehydes and
thioketones, which could be isolated as their cycloadducts with dienes. The use of
CF3SO3SiMe3 in reactions with cyclohexadiene allows a stereopredetermined access to either the
endo- or the exo-isomer. Furthermore, on using β-silyl-substituted acetylenic ketones, a smooth access
to acetylenic thioketones can be achieved. In reactions with aromatic and heteroaromatic
o-azido aldehydes, the reactivity of HMDST may be finely tuned toward the synthesis
of o-azido thioaldehydes, fused isothiazole ring systems, aromatic and heteroaromatic
o-amino aldehydes, and o-amino thioaldehydes.
HMDST proved also very efficient in thionating more intriguing substrates such as
acylsilanes. Thus, thioacylsilanes, thioformylsilanes, unsaturated thioacylsilanes
and -stannanes can be obtained in good yields. Ethylenic thioacylsilanes showed an
interesting behavior leading to a general synthesis of functionalized dithiins. Finally,
HMDST led also to the synthesis of bis(thioacylsilanes), which led to the formation
of new silylated thiaheterocyclic systems.
-
1 Introduction
-
2 HMDST-Based Synthesis of Thiocarbonyl Compounds
-
2.1 Thioaldehydes and Thioketones
-
2.2 α,β-Unsaturated Thiocarbonyl Compounds
-
3 Tuning of the Chemical Behavior of Azido Aldehydes
-
3.1 Azido Thioaldehydes
-
3.2 Isothiazoles
-
3.3 Amino Aldehydes
-
3.4 Amino Thioaldehydes
-
4 Reactivity of Amino Thioaldehydes
-
5 Thioacylsilanes and Thioacylstannanes
-
5.1 Synthesis of Thioacylsilanes and Thioformylsilanes
-
5.2 α,β-Unsaturated Thioacylsilanes
-
5.3 α,β-Unsaturated Thioacylstannanes
-
5.4 Bis(thioacylsilanes)
-
6 Conclusions
Key words
silyl sulfides - cycloadditions - thiocarbonyl componds - heterocycles - heterodienes
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