Ethyl-2- methylthio -8-hexyloxocane

To a stirred solution of ( )-8-hexyl-2-oxocanethione (prepared from the reaction of the lactone and Lawesson s reagent as in Section 2.8.3) (126 mg, 0.55 mmol) in anhydrous THF (6ml) at -78°C was added, under 

The preceding compound (125 mg, 0.46mmol) was sliued together with triphenyltin hydride (0.29 mmol, 1.15 mmol) and AIBN (5 mg) in toluene (8ml) at reflux temperature for 20 min. Concentration and silica gel chromatography (2% ether in petroleum ether) gave the title ether (95.6 mg, 92%). 

One case of thiophilic addition has been reported for a bisthionester [356]  

This fits with the general tendency for thiophilic addition to be favoured by a strong withdrawing group a to the thiocarbonyl function [328]. 

As mentioned before, it was with thioketones that the first cases of thiophilic addition were evidenced, but many other modes of reaction have been observed concurrently carbophilic addition, reduction, coupling, double addition, and enethiolization [357], We will not discuss these reactions here, which have not been used much for synthetic purposes. 

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