Prescursors for and synthesis of mono- and difunctionalized acetylenes and difunctional 1,3-diynes

• Main Authors: ZHDANKIN; VIKTOR, STANG; PETER J, CRITTELL; CHARLES M, WILLIAMSON; BOBBY L
• Format: Patent
• Language: English
• Published: 15.02.1994
• Edition: 5
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY

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+(X)OSO2Rf, 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+C(triple bond)CI+Ph(solid dot)2 RfSO3-,a mixed iodonium sulfonate is reacted with a bistin acetylene of the kind R'3SnC(triple bond)CSnR"3. Alternatively, the reaction may be performed with disubstituted tin diacetylenes to produce PhI+C(triple bond)C-C(triple bond)CI+Ph(solid dot)2 RfSO3-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.