1-(organosulfonyloxy)-3(1H)-1,2-benziodoxoles: Preparation and reactions with alkynyltrimethylsilanes

Viktor Zhdankin, Chris J. Kuehl, Alexei P. Krasutsky, Jason T. Bolz, Angela J. Simonsen

Research output: Contribution to journalArticle

102 Scopus citations

Abstract

Organosulfonyloxy derivatives of 1,2-benziodoxol-3(1H)-one (3a-c) and 3,3-bis(trifluoromethyl)-3(1H)-1,2-benziodoxole (5a-c) can be prepared in high yield by the reaction of 1-hydroxybenziodoxoles 1 or 4 and the corresponding sulfonic acids or Me3SiOTf in the form of stable, but moderately hygroscopic, microcrystalline solids. Reaction of the triflate derivatives 3a and 5a with alkynyltrimethylsilanes affords either alkynyliodonium triflates 6, or (E)-β-(trifluoromethanesulfonyloxy)-alkenyliodonium triflates 7, while the same reaction in the presence of pyridine selectively gives the respective 1-alkynylbenziodoxoles 8 and 9 in 82-90% yield.

Original languageEnglish (US)
Pages (from-to)6547-6551
Number of pages5
JournalJournal of Organic Chemistry
Volume61
Issue number19
StatePublished - Sep 20 1996

    Fingerprint

Cite this

Zhdankin, V., Kuehl, C. J., Krasutsky, A. P., Bolz, J. T., & Simonsen, A. J. (1996). 1-(organosulfonyloxy)-3(1H)-1,2-benziodoxoles: Preparation and reactions with alkynyltrimethylsilanes. Journal of Organic Chemistry, 61(19), 6547-6551.