13892-81-4Relevant articles and documents
Highly Efficient Gold(I)-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Internal Alkynes
Dupuy, Stéphanie,Gasperini, Danila,Nolan, Steven P.
, p. 6918 - 6921 (2015)
We report the highly efficient gold-catalyzed hydrocarboxylation of internal alkynes that operates under solvent- and silver-free conditions. This new, simple, and eco-friendly protocol allows for the synthesis of a wide variety of functionalized aryl and
Stereochemistry of the Acetoxymercuration of Alkynes. A Synthesis of Vinyl Acetates
Bach, Robert D.,Woodard, Robert A.,Anderson, Thomas J.,Glick, Milton D.
, p. 3707 - 3712 (1982)
The stereochemistry of acetoxymercuration of 3-hexyne has been established as antarafacial on the basis of an X-ray crystallographic study.Acetoxymercuration of diphenylacetylene afforded (Z)-α-acetoxy-β-(acetoxymercuri)stilbene by a suprafacial addition of Hg(OAc)2.A simple method for the in situ acetoxymercuration-demercuration of dialkyl-substituted alkynes to afford vinyl acetates is described.The sodium borohydride reduction of vinyl mercurials was shown to produce divinyl mercurials while demercuration with zinc dust in acetic acid provided a useful method for the preparation of vinyl acetates.
Electron-Transfer Photosensitized Oxygenation of Stilbene and Naphthalene Derivatives in the Presence of Acetate Ion. Controlling the Reaction of the Cation Radicals by Weak-Nucleophilic Salts
Yamashita, Toshiaki,Tsurusako, Taiji,Nakamura, Nobuya,Yasuda, Masahide,Shima, Kensuke
, p. 857 - 862 (2007/10/02)
The 9,10-Dicyanoanthracene (DCA)- or 9-cyanoanthracene-sensitized photooxygenation of trans-stilbene derivatives gave benzaldehyde derivatives efficiently in the presence of weak-nucleophilic salts, such as Et4NOAc and KOAc/18-crown-6 ether.The product distribution of this photooxygenation was apparently different from that of each photooxygenation in the presence of Mg(ClO4)2 and Et4NBF4 or in the absence of the salt.The DCA-sensitized photooxygenation of 2-methylnaphthalene gave phthalic acid and 4-methylphthalic acid in the presence of Nt4NOAc.These products were different from the products generated from each photooxygenation in the presence of Et4NBF4 and KClO4 or in the absence of the salt.Also, such ring-oxygenation occurred in the DCA-sensitized photooxygenation of 2,3-dimethylnaphthalene and naphthalene in the presence of Et4NOAc.These photooxygenations in the presence of Et4NOAc proceeded by the addition of an acetate ion to the cation radical of the substrate generated by a photochemical electron transfer from the substrate to the sensitizer and the subsequent reaction with O2 and the related oxygen species.