Thione-Thiol Tautomerism and Its Application to Organic Synthesis

Thione-Thiol Tautomerism and Its Application to Organic Synthesis 

As shown in the previous sections, pyridine and related azaaromatic compounds possess a strong electron-withdrawing property equivalent to thep-nitrophenyl group and hence serve as good leaving groups. The facile 

Katritzky et al. reported that alkyl halides convert to thiols in one pot when treated with a thiopyridine, which initially transforms to the pyridi-nium salt (34). Intramolecular ipsosubstitution takes place in the s t (34) by the remote hydroxyl group to afford the corresponding thiols shown in reaction (49) (85TL469). Thus, pyridinium sulfides readily undergo both 

Asymmetric induction using an optically active acrylate ester with O-ethylthiohydroxamate has also been reported (87TL4205). [See reaction (52).] A review on the photolysis and thermolysis of O-hydroxamic thio- 

The chemistry of both organic sulfur compounds and azaaromatic compounds has been widely investigated mainly for industrial purposes for many years, and vast amounts of data have been accumulated. However, many studies lack mechanistic support. 

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IV. Thione-Thiol Tautomerism and Its Application to Organic Synthesis. 43... 

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