Mechanism of the cyclization of dimethyl diethynyl silane with selenium tetrabromide: Computational and structural studies, and monitoring

The reaction of selenium dichloride with divinyl sulfide

“…This reaction was performed with various diorganyl diethynyl silanes and germanes providing previously unknown 1-selena-4-silafulvenes and 4-germafulvenes [13][14][15][16][17][18].…”

Quantum chemical studies of the reaction of selenium dichloride with divinyl sulfide and comparison with experimental results

“…The reaction was performed with various diorganyl diethynyl silanes and -germanes and provided previously unknown 1-selena-4-silafulvenes and 1-selena-4-germafulvenes [3][4][5][6][7][8].…”

“…In spite of the fact, that selenium dichloride and dibromide exist in equilibrium with other selenium species, these reagents can be used in reactions to give organoselenium compounds with good selectivity and in high yield [1][2][3][4][5][6][7][8].…”

“…As part of our continued investigations of reactions of selenium halides with organic compounds [1][2][3][4][5][6][7][8]13] we have recently studied the addition reaction of selenium dichloride (2) to divinyl sulfide (1) [14]. We found that the reaction at À50°C in chloroform afforded 2,6-dichloro-1,4-thiaselenane (3), in virtually quantitative yield (Scheme 1).…”

“…At room temperature in chloroform solution, thiaselenane 3 underwent spontaneous rearrangement to 5-chloro-2-chloromethyl-1,3-thiaselenolane (4). A mechanism of the rearrangement was supposed to involve seleniranium cation [14].…”