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Issue 12, 2013
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Iodine-catalyzed disproportionation of aryl-substituted ethers under solvent-free reaction conditions

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Abstract

Iodine was demonstrated to be an efficient catalyst for disproportionation of aryl-substituted ethers under solvent-free reaction conditions. Variously substituted 1,1,1′,1′-tetraaryldimethyl ethers were transformed into the corresponding diarylketone and diarylmethane derivatives. I2-catalyzed transformation of 4-methoxyphenyl substituted ethers yielded mono- and dialkylated Friedel–Crafts products as well. Treatment of trityl alkyl and trityl benzyl ethers with a catalytic amount of iodine produced triphenylmethane and the corresponding aldehydes and ketones. The electron-donating substituents facilitated the reaction, while the electron-withdrawing groups retarded it; the difference in reactivity is not very high. Such an observation may be in favour of hydride transfer, predominantly from the less electron rich side of the ether with more stable carbocation formation. With the isotopic studies it was established that a substantial portion of the C–H bond scission took place in the rate-determining step, while the carbonyl oxygen atom originated from the starting ether, and not from the air. The transformation took place under air and under argon, and HI was not a functioning catalyst.

Graphical abstract: Iodine-catalyzed disproportionation of aryl-substituted ethers under solvent-free reaction conditions

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The article was received on 22 Nov 2012, accepted on 11 Jan 2013 and first published on 14 Jan 2013


Article type: Paper
DOI: 10.1039/C3OB27267B
Org. Biomol. Chem., 2013,11, 1978-1999

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    Iodine-catalyzed disproportionation of aryl-substituted ethers under solvent-free reaction conditions

    M. Jereb and D. Vražič, Org. Biomol. Chem., 2013, 11, 1978
    DOI: 10.1039/C3OB27267B

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