EXCHANGE OF CARBON LIGANDS AT IODINE IN IODONIUM SALTS. A DIRECT SYNTHESIS OF ARYL(2-FURYL)IODONIUM TOSYLATES FROM ARYL(TERT-BUTYLETHYNYL)IODONIUM TOSYLATES
EXCHANGE OF CARBON LIGANDS AT IODINE IN IODONIUM SALTS. A DIRECT SYNTHESIS OF ARYL(2-FURYL)IODONIUM TOSYLATES FROM ARYL(TERT-BUTYLETHYNYL)IODONIUM TOSYLATES
复制标题
碘盐中碳配体与碘的交换。
DOI：
10.1002/chin.198521158
复制
发表时间：
1985
期刊：
影响因子：
--
通讯作者：
G. Koser
中科院分区：
文献类型：
--
作者：
Anthony J. Margida;G. Koser
Various [hydroxy (tosyloxy) iodo] arenes (RC6H4I (OH) OTs, R= H, 2-Me, 3-Me, 4-Me, 2-F, 3-F, 4-F, 2-C1, 3-C1) have been found to react with tert-butylacetylene in chloroform under reflux to give the corresponding aryl-(tert-butylethynyl) iodonium tosylates (Me3CC^ CI+ C6H4R" OTs) in yields ranging from 56% to 80%. When the arylethynyl salts (R= 2-Me, 3-Me, 4-Me, 2-F, 3-F 4-F, 3-C1) were mixed with 2-lithiofuran in ether-hexane and treated subsequently with p-TsOH-H20 in ether, the corresponding aryl (2-furyl) iodonium tosylates were obtained in yields ranging from 21% to 74%. 2-Lithiofuran reacted similarlywith phenyl (phenylethynyl) iodoniumtosylate to give a 60% yield of (2-furyl) phenyliodonium iodide (after HC1 quenching and KI treatment). The exchange reaction is not limited to 2-lithiofuran. Thus,(íert-butylethynyl)(2-methylphenyl) iodoniumtosylate reacted with 2-lithiothiophene and with 2-lithio-5-methylthiophene to give the corresponding (2-methylphenyl)(2-thienyl) iodonium tosylates in 62% and 64% yields, respectively.(tert-Butylethynyl) phenyliodonium tosylate reacted similarly with 2-lithiothianaphthene to give a 70% yield of phenyl (2-thianaphthenyl) iodonium tosylate.
