Preparation and chemistry of phi+c=ci+ph•2otf, bis[phenyl[[(trifluoromethyl)sulfonyl]oxy]iodo]acetylene, a novel difunctional acetylene, bis(iodonium) species and a stable c2-transfer agent

Peter J. Stang, Viktor V. Zhdankin

Research output: Contribution to journalArticle

86 Scopus citations

Abstract

The title compound 2 is readily prepared as a stable microcrystalline solid from bis(tri-n-butylstannyl)acetylene and PhlCN•OTf. It was fully characterized by multinuclear NMR, IR, and elemental analysis. As expected, the electron-deficient acetylene 2 reacts with a number of nucleophiles (e.g., Ph3P, PhSNa, and PhOLi) providing a variety of bifunctionalized acetylenes 5, 6, 7, and 9. It also undergoes cycloaddition reactions with cyclopentadiene, furan, and other 1,3-dienes to afford useful bis(iodonium)norbornadiene-type adducts 12–14.

Original languageEnglish (US)
Pages (from-to)4571-4576
Number of pages6
JournalJournal of the American Chemical Society
Volume113
Issue number12
DOIs
StatePublished - Jun 1 1991

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