Rearrangement of the tert-butyl group of 5,6-di-tert-butyl-2,3,7-trithiabicylo-5-ene 7-endoxide

Treatment of 5,6-di-tert-butyl-2,3,7-trithiabicylo-5-ene 7-endoxide with trimethylsilyl trifluoromethanesulfonate at room temperature resulted in the rearrangement of tert-butyl group to furnish 4,6-di-tert-butyl-2,3,7-trithiabicylo-5-ene 7-endoxide quantitatively. Meanwhile, treatment of the compou...

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Bibliographic Details
Published in:Journal of sulfur chemistry 2008-02, Vol.29 (1), p.1-7
Main Authors: Yoshida, Sanae, Morohashi, Yuta, Fujihara, Takashi, Sugihara, Yoshiaki, Nakayama, Juzo
Format: Article
Language:English
Subjects:
1,2-dithiin
2,3,7-trithiabicylo-5-ene 7-oxide
rearrangement
trimethyloxonium tetrafluoroborate
trimethylsilyl trifluoromethanesulfonate
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Summary:Treatment of 5,6-di-tert-butyl-2,3,7-trithiabicylo-5-ene 7-endoxide with trimethylsilyl trifluoromethanesulfonate at room temperature resulted in the rearrangement of tert-butyl group to furnish 4,6-di-tert-butyl-2,3,7-trithiabicylo-5-ene 7-endoxide quantitatively. Meanwhile, treatment of the compound by trimethyloxonium tetrafluoroborate afforded 4,5-di-tert-butyl-1,2-dithiin 1,1-dioxide in addition to the above rearrangement product.
ISSN:1741-5993
1741-6000
DOI:10.1080/17415990701753373