The reaction of bis(trimethylsilyl) sulfide with substituted thiiranes under tetrabutylammonium fluoride catalysis leads to the synthesis of 3,7-disubstituted-1,2,5-trithiepanes, through regioselective reaction of a thiosilane intermediate with another molecule of episulfide, followed by intramolecular oxidation of two sulfur units. When using bis(trimethylsilyl)selenide, the reaction with thiiranes and TBAF affords a smooth access to a novel class of disubstituted-1,2,5-dithiaselenepanes.
Thiosilane- and organoselenosilane-mediated novel access to 3,7-disubstituted-1,2,5- trithiepanes and -1,2,5-dithiaselenepanes / Antonella Capperucci; Damiano Tanini; Cosimo Borgogni; Alessandro DeglInnocenti. - In: HETEROATOM CHEMISTRY. - ISSN 1042-7163. - STAMPA. - 25:(2014), pp. 678-683. [10.1002/hc.21157]
Thiosilane- and organoselenosilane-mediated novel access to 3,7-disubstituted-1,2,5- trithiepanes and -1,2,5-dithiaselenepanes
CAPPERUCCI, ANTONELLA;TANINI, DAMIANO;
2014
Abstract
The reaction of bis(trimethylsilyl) sulfide with substituted thiiranes under tetrabutylammonium fluoride catalysis leads to the synthesis of 3,7-disubstituted-1,2,5-trithiepanes, through regioselective reaction of a thiosilane intermediate with another molecule of episulfide, followed by intramolecular oxidation of two sulfur units. When using bis(trimethylsilyl)selenide, the reaction with thiiranes and TBAF affords a smooth access to a novel class of disubstituted-1,2,5-dithiaselenepanes.
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