Regio- and stereoselective synthesis of new ensembles of diversely functionalized 1,3-thiaselenol-2-ylmethyl selenides by a double rearrangement reaction

• Svetlana V. Amosova,
• Andrey A. Filippov,
• Nataliya A. Makhaeva,
• Alexander I. Albanov and
• Vladimir A. Potapov

Beilstein J. Org. Chem. 2020, 16, 515–523, doi:10.3762/bjoc.16.47

• Svetlana V. Amosova Andrey A. Filippov Nataliya A. Makhaeva Alexander I. Albanov Vladimir A. Potapov A. E. Favorsky Irkutsk Institute of Chemistry, SD RAS, 1 Favorsky Str., 664033 Irkutsk, Russian Federation 10.3762/bjoc.16.47 Abstract The reaction of 2-(bromomethyl)-1,3-thiaselenole with

• , we are observing a new manifestation of this effect, consisting in the promotion of new rearrangements leading to the selective formation of various selenium-containing unsaturated linear and heterocyclic compounds. This effect works in 2-(bromomethyl)-1,3-thiaselenole (1) – a unique reagent, which

• ppm (for the ring) and 148.82–401.09 ppm (in the side chain). Conclusion The reaction of 2-(bromomethyl)-1,3-thiaselenole (1) with potassium selenocyanate was found to occur with a rearrangement and ring expansion leading to six-membered 2,3-dihydro-1,4-thiaselenin-2-yl selenocyanate 5, which at room