Oxidative rearrangement of alkynes to carboxylic acid esters by [Hydroxy(tosyloxy)iodo]benzene in methanol
作者： Robert M Moriarty , Radhe K Vaid , Michael P Duncan , Beena K Vaid
DOI: 10.1016/S0040-4039(00)96224-5
关键词: Aliphatic compound 、 Oxidative phosphorylation 、 Carboxylic acid 、 Chemistry 、 Organic chemistry 、 Hydrocarbon 、 Benzene 、 Aryl 、 Hydrolysis 、 Methanol
摘要: Abstract A direct synthesis of methyl aryl alkanoate via oxidative rearrangement alkynes using [hydroxy(tosyloxy)iodo]benzene in methanol is described.
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Peter J. Stang, Bruce W. Surber, Zhen Chu Chen, Kenneth A. Roberts, Albert G. Anderson, Acetylenic esters. Preparation and mechanism of formation of alkynyl tosylates and mesylates via tricoordinate iodonium species Journal of the American Chemical Society. ,vol. 109, pp. 228- 235 ,(1987) , 10.1021/JA00235A034
Robert M. Moriarty, Steven C. Engerer, Om Prakash, Indra Prakash, Udai S. Gill, Wade A. Freeman, Stereoselection in the hypervalent iodine oxidation of chromium tricarbonyl complexes of benzocyclanones Journal of Organic Chemistry. ,vol. 52, pp. 153- 155 ,(1987) , 10.1021/JO00377A028
Yasumitsu Tamura, Takayuki Yakura, Jun-ichi Haruta, Yasuyuki Kita, An efficient conversion of keto groups into dihydroxyacetone groups: Oxidation of ethynylcarbinol intermediates by using hypervalent iodine reagent Tetrahedron Letters. ,vol. 26, pp. 3837- 3840 ,(1985) , 10.1016/S0040-4039(00)89264-3
Anthony J. Margida, Gerald F. Koser, EXCHANGE OF CARBON LIGANDS AT IODINE IN IODONIUM SALTS. A DIRECT SYNTHESIS OF ARYL(2-FURYL)IODONIUM TOSYLATES FROM ARYL(TERT-BUTYLETHYNYL)IODONIUM TOSYLATES Journal of Organic Chemistry. ,vol. 49, pp. 4703- 4706 ,(1984) , 10.1021/JO00198A023
Louis Rebrovic, Gerald F. Koser, ALKYNYLARYLIODONIUM TOSYLATES AND ARYL(β-(TOSYLOXY)VINYL)IODONIUM TOSYLATES FROM REACTIONS OF TERMINAL ALKYNES WITH (HYDROXY(TOSYLOXY)IODO)BENZENE Journal of Organic Chemistry. ,vol. 49, pp. 4700- 4702 ,(1984) , 10.1021/JO00198A022
Robert M. Moriarty, Om Prakash, Michael P. Duncan, Radhe K. Vaid, Hikmat A. Musallam, Hypervalent iodine oxidation of silyl enol ethers under Lewis-acid conditions in methanol. A general route to .alpha.-methoxy ketones Journal of Organic Chemistry. ,vol. 52, pp. 150- 153 ,(1987) , 10.1021/JO00377A027
Paul Müller, José Godoy, Ru-Catalyzed Oxidation of Acetylenes to α-Diketones with Iodosylbenzene Helvetica Chimica Acta. ,vol. 64, pp. 2531- 2533 ,(1981) , 10.1002/HLCA.19810640807
Peter J. Stang, Manfred. Boehshar, Jing. Lin, Acetylenic esters. Preparation and characterization of hitherto unknown alkynyl carboxylate, RC.tplbond.COCOR1, and alkynyl phosphate, RC.tplbond.COPO(OR1)2, esters. Journal of the American Chemical Society. ,vol. 108, pp. 7832- 7834 ,(1986) , 10.1021/JA00284A057
Teruo Umemoto, Yuriko Kuriu, Osamu Miyano, Perfluoroalkylation of alkynes with RfI(Ph)OSO2CF3 Tetrahedron Letters. ,vol. 23, pp. 3579- 3582 ,(1982) , 10.1016/S0040-4039(00)87675-3
F. Marshall Beringer, Suzanne A. Galton, Acetylenic and Ethylenic Iodonium Salts and Their Reactions with a Carbanion1,2 The Journal of Organic Chemistry. ,vol. 30, pp. 1930- 1934 ,(1965) , 10.1021/JO01017A053