Sodium pyridine-2-thiolate, reaction

Dichloropyridines were converted in good yield to the corresponding bis(alkylthio)pyridines via reaction with sodium thiolates in DMF at 140 C.185 Room temperature oxidation of the sulfides with chlo-rax solution gave bis(alkylsulfonyl)pyridines in high yields.185... 

Analogous substitution reactions take place with alkane- and arene-thiolate anions <73JCS(P1)16S9), and pyridine-2- and -4-thiones are usually prepared by use of sodium or potassium hydrogen sulfide or thiourea (74JCS(P1)2300). 

Zakharkin and co-workers have studied, in detail, the synthesis and reactions of fluorovinyl-substituted carbaboranes (Vol. 1, p. 89). In Scheme 12 are shown some of the reactions described. Apparently the ability of the o-carbaboranyl nucleus to stabilize a negative charge during nucleophilic addition-elimination reactions exceeds that of either chlorine or trifluoro-methyl, attack on the double bond occurring p to the nucleus. > 4,4-Dichloro-3,3-difluoro-l-phenylcyclobutene reacts with aryl-lithium compounds, sodium thiolates NaSAr (Ar = Ph,p-MeC,H4,orn-H2N-CeH4), or pyridine or other heterocyclic bases by substitution with rearrangement. 

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