Phase transfer catalytic synthesis of silyl derivatives of heterocyclic thiols
Reactions of heteroaromatic thiols with trialkylsilylalkyl iodides in the two-phase catalytic system (solid K2CO3/18-crown-6/toluene) at 111°C selectively lead to formation of the corresponding (trialkylsilylalkyl)thiohetarenes. 6-Me
Modelling nucleophilic substitution at silicon in solution using hypervalent silicon compounds based on 2-thiopyridones
Halodimethylsilylmethyl derivatives of 2-thiopyridones have been prepared. The N-CH2 isomer is favoured with the 6-methylthiopyridone. 13C and 29Si chemical shifts have been used to calculate the extent of sulfur-silicon bond formation and the extent of pentacoordination. The results are consistent with the oxygen analogues and reveal that as expected sulfur is a poorer nucleophile than oxygen. The unsubstituted thiopyridone and the 5-trifluoromethyl derivative favour the S-CH2 isomer. Again the mapping of nucleophilic substitution by nitrogen is in line with sulfur and oxygen nucleophiles, but in this series nitrogen is a poorer nucleophile than expected. The results are discussed in terms of steric strain, the preferences for alkylation of the pyridones and the bond strength of coordination to silicon.
Bassindale, Alan R.,Parker, David J.,Taylor, Peter G.
p. 1059 - 1066
(2007/10/03)
REACTION OF 2-TRIMETHYLSILYLMETHYLTHIOPYRIDINE PROMOTED BY A FLUORINE ION: THE FIRST EXAMPLE OF GENERATION OF 2-PYRIDYLTHIOMETHYLCARBANION
2-Trimethylsilylmethylthiopyridine prepared readily by the reaction of 2-mercaptopyridine with chloromethyltrimethylsilane in the presence of potassium carbonate reacts with carbonyl compounds in the presence a catalytic amount of tetrabutylammonium fluor
Kohra, Shinya,Ueda, Hiroshi,Tominaga, Yoshinori
p. 1497 - 1500
(2007/10/02)
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