1073253-91-4Relevant academic research and scientific papers
Stereospecific cyclodehydration of 1,4-sulfanylalcohols to thiolanes: mechanistic insights
Filippi, Jean-Jacques,Du?ach, Elisabet,Fernandez, Xavier,Meierhenrich, Uwe J.
, p. 9999 - 10003 (2008)
A series of thiolanes were prepared by cyclodehydration of sulfanylalcohols in the presence of catalytic amounts of p-toluenesulfonic acid or by using K10 clay. The sulfur heterocycles were synthesised in good to excellent yields using either a conventional Dean-Stark method or microwave irradiation under solvent-free conditions. The reaction could be performed regio- and stereoselectively and its mechanism was investigated by means of enantio- and diastereomerically enriched substrates. In contrast to previous studies, our results are consistent with an intramolecular SN2-type mechanism as a general pathway.
