Add time:07/31/2019         Source:sciencedirect.com

Regio- and stereoselective reactions of 2-bromomethyl-1,3-thiaselenole with water and ethylene glycol are accompanied by a rearrangement with the expansion of the five-membered ring to six-membered 2,3-dihydro-1,4-thiaselenine derivatives. The reactions proceed under unusually mild conditions at room temperature presumably via seleniranium intermediates involving a series of unexpected cascade transformations. First representatives of unsaturated polyfunctional 2,3-dihydro-1,4-thiaselenines bearing O-, S- and Se-containing substituents were obtained in up to 80% yield.

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