Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfonic acids or salts thereof
Patent
1991-07-19
1994-02-15
Dees, Jose G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Sulfonic acids or salts thereof
562 45, 562 83, 562 85, C07C30900
Patent
active
052869016
ABSTRACT:
Precursors and methods for the synthesis of mono- and difunctionalized acetylenes are described. The invention includes novel tricoordinate iodonium transfer reagents and novel alkynyldi(phenyliodonium) salts, both of which are precursors for the functionalized acetylenes. The iodonium transfer reagents take the general form of mixed iodonium sulfonates PhI.sup.+ (X)OSO.sub.2 R.sub.f, where X may be OAc, NHAc, NCO, or CN. These mixed iodonium sulfonates are produced by reaction of iodosobenzene with certain substituted trimethylsilanes.
To make the alkynyldi(phenyliodonium) salt PhI.sup.+ C.tbd.CI.sup.+ Ph.cndot.2 R.sub.f SO.sub.3.sup.-,a mixed iodonium sulfonate is reacted with a bistin acetylene of the kind R'.sub.3 SnC.tbd.CSnR".sub.3. Alternatively, the reaction may be performed with disubstituted tin diacetylenes to produce PhI.sup.+ C.tbd.C-C.tbd.CI.sup.+ Ph.cndot.2 R.sub.f SO.sub.3.sup.- to produce a dialkynyldi(phenyliodonium) salt. Subsequent reaction of a nucleophile with the alkynyldi(phenyl-iodonium) salt or dialkynyldi(phenyliodonium) salt produces a difunctional acetylene or a difunctional 1,3-diyne, respectively.
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Crittell Charles M.
Stang Peter J.
Williamson Bobby L.
Zhdankin Viktor
Conrad Joseph
Dees Jos,e G.
University of Utah Research Foundation
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