xxxxx
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i,i dimethyl iodobenzene
i was interested in whether it may possible to produce i,i dimethyl iodobenzene (where both methyl groups are on the iodine). supposedly i,i dichloro
iodobenzene could be formed according to organic synthesis then methyllithium could be added. maybe someone could tell me if this would or would not
work, or if there might be an easier method.
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majdo
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This problem refers to hypervalent iodine chemistry and it's quite fresh topic.Never heard of something like iodine bonded with 3 carbons.My intuition
 says that your proposition of preparation is highly unlikely.
That Which Is Not Dead Which Can Eternally Lie And With Strange Aeons Even Death May Die
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Nicodem
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Methyl groups are not electronegative enough to keep iodine in the +3 oxidation state.
Therefore the reaction of 2 equivalents of MeLi with PhICl2 would be very violent and exothermic. If tempered with cold and dilution it should result
in iodobenzene, LiCl and some oxidation byproducts of methyl lithium (ethane probably).
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
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unionised
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"This problem refers to hypervalent iodine chemistry and it's quite fresh topic.Never heard of something like iodine bonded with 3 carbons"
The corresponding fluoride and chloride are discussed in Sidgwick's "chemical elements and their compounds" published in 1950, though I accept that's
not the same as a trialkyl iodine.
I guess Nicodem is probably right about the dimethyl version but I wouldn't be suprised if there were a bis trifluoromethyl compound. Certainly,
simple electronegativity arguments can't rule out I(C6H5)3
[Edited on 26-2-2006 by unionised]
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majdo
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You are right.I got some old books that describe these compounds are KNOWN for some time,however interest in them has been developed recently.These
are derivatives of iodobenzene.Two of three iodine bonds(or 4 of 5 if iodine is pentavalent) are with most electronegative elements (O,N and Cl of
course like here).There are some publications i.e on
www.organic-chemistry.org
That Which Is Not Dead Which Can Eternally Lie And With Strange Aeons Even Death May Die
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unionised
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Of course, the important thing is that, young, old, or indifferent, these things are interesting.
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