- Conversion of Olefins to Ditriflates by μ-Oxobis
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A new preparation of μ-oxobis, 1, from iodosobenzene and triflic anhydride is reported.The use of 1 provides a mild, single-step procedure for the conversion of olefins to vicinal ditriflates and of dienes to 1,4
- Hembre, Robert T.,Scott, Carl P.,Norton, Jack R.
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- Synthesis and reactivity of aryl(alkynyl)iodonium salts
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The first practical, yet simple, preparation of aryl(alkynyl)iodonium trifluoroacetate salts is described. The generic nature of this synthetic method has allowed the production of a range of aryl(alkynyl)iodonium trifluoroacetate salts with independent variation of both the alkynyl and aryliodo groups in yields of 30-85 %. Application of these new reagents to the synthesis of a series of 2-arylfuro[3,2-c]pyridines (40-64 %) highlights the potential of this class of materials as precursors to bioactive heterocyclic structures. These experiments have also demonstrated that, in this case, the effect of the aryliodo group on the reaction is negligible.
- Dixon, Luke I.,Carroll, Michael A.,Gregson, Thomas J.,Ellames, George J.,Harrington, Ross W.,Clegg, William
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p. 2334 - 2345
(2013/05/21)
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- Generation and trapping reactions of 1-tert-butoxycarbonyl-3,4-didehydro-1H-pyrrole
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3,4-Bis(trimethylsilyl)-1H-pyrrole (5) was employed as a key precursor to generate a highly strained and reactive five-membered cyclic cumulene, namely 1-tert-butoxycarbonyl-3,4-didehydro-1H-pyrrole (4). The transient existence of 4 at room temperature was confirmed by trapping reactions with furan, acrylonitrile, and benzene, affording cycloadducts 13-15. The choice of the electron-withdrawing tert-butoxycarbonyl group as the N-substituent was essential because it was able to adjust the electron density of 11a and 11b. As a result, monoiodonium triflates 12a and 12b were obtained, respectively. On the contrary, N-tert-butyl-3,4-bis(trimethylsilyl)-1H-pyrrole (9) led instead to the bisiodonium triflate 10 upon treatment with the Zefirov reagent.
- Liu, Jian-Hui,Chan, Ho-Wai,Feng, Xue,Wang, Qi-Guang,Mak, Thomas C. W.,Wong, Henry N. C.
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p. 1630 - 1634
(2007/10/03)
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- Synthesis of Alkynyl(phenyl)iodonium Triflates and Their Reaction with Diethyl 2-Aminomalonate
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Alkynyl(phenyl)iodonium triflates 9 react with the Li (or K) salt of diethyl 2-malonate (10) (M = Li or K) to give the corresponding diethyl 2-alkynyl-2-malonate (11) in 30 - 95 percent yield.
- Bachi, Mario D.,Bar-Ner, Nira,Crittell, Charles M.,Stang, Peter J.,Williamson, Bobby L.
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p. 3912 - 3915
(2007/10/02)
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- NOVEL REAGENTS CONTAINING HYPERVALENT IODINE AND THEIR USE FOR ELECTROPHILIC ADDITIONS TO OLEFINS
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A series of novel I(III) containing reagents have been developed and their electrophilic reactions with olefins giving vic-disubstituted derivatives (including vic-ditriflates) are described.
- Zefirov, Nikolai S.,Zhdankin, Viktor V.,Dan'kov, Yu. V.,Caple, Ronald,Berglund, Bruce A.
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p. 3971 - 3974
(2007/10/02)
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