Thiosilane‐ and Organoselenosilane‐Mediated Novel Access to 3,7‐Disubstituted‐1,2,5‐ trithiepanes and ‐1,2,5‐dithiaselenepanes | Zendy

Capperucci Antonella | Zendy; Tanini Damiano | Zendy; Borgogni Cosimo | Zendy; DegľInnocenti Alessandro | Zendy

Open Access

Thiosilane‐ and Organoselenosilane‐Mediated Novel Access to 3,7‐Disubstituted‐1,2,5‐ trithiepanes and ‐1,2,5‐dithiaselenepanes

Author(s) -

Capperucci Antonella,

Tanini Damiano,

Borgogni Cosimo,

DegľInnocenti Alessandro

Publication year - 2014

Publication title -

heteroatom chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.283

H-Index - 42

eISSN - 1098-1071

pISSN - 1042-7163

DOI - 10.1002/hc.21157

Subject(s) - chemistry , trimethylsilyl , selenide , intramolecular force , sulfide , regioselectivity , fluoride , sulfur , medicinal chemistry , catalysis , allylic rearrangement , combinatorial chemistry , organic chemistry , selenium , inorganic chemistry

The reaction of bis(trimethylsilyl) sulfide with different substituted thiiranes under tetrabutylammonium fluoride (TBAF) 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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