Arbacluce
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Synthesis and properties of I-NO2.
Hi,
I know that this compund exist and it can by made by the reaction of sodium nitrite or silver nitrite with iodine but If it is easy to make I-Cl by
combining iodine with chlorine gas it should be also possible to synthesise I-NO2 by combining NO2 gas with elemental iodine. That compund would be
very strong electrophile and(I think) very good iodinating agent in electrophilic aromatic substitution. What do you think?
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j_sum1
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Coincidentally, chemplayer just released a video on synthesis of ICl. I'll let you decide if that is straightforward.
As for synths with it, that is beyond my knowledge. But he did make 3,5 iodo salcicylic acid. You might find it interesting.
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wg48
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Quote: Originally posted by Arbacluce  | Hi,
I know that this compund exist and it can by made by the reaction of sodium nitrite or silver nitrite with iodine but If it is easy to make I-Cl by
combining iodine with chlorine gas it should be also possible to synthesise I-NO2 by combining NO2 gas with elemental iodine. That compund would be
very strong electrophile and(I think) very good iodinating agent in electrophilic aromatic substitution. What do you think? |
Preparative Methods: iodine nitrate (INO3) and iodine nitrite (INO2, more appropriately called nitryl iodide) often show similar chemical properties
and can be prepared in situ from iodine and silver nitrate or silver nitrite, respectively. The first reported4 preparation of INO3 was from
Mercury(II) Nitrate and Iodine in ether. Silver(I) Nitrate and I2 in ether, acetonitrile, or MeOH, as well as AgNO3 and Iodine Monochloride in
CHCl3–pyridine, have been used successfully for additions to alkenes,1, 4 although the latter reagent also leads to iodopyridinium adducts.1
Nitrogen Dioxide and I2 have also been used to generate INO3.2 The first reports7 of INO2 addition to alkenes employed Silver(I) Nitrite and I2 in
ether to produce iodo nitro adducts, but this reagent also can lead to INO3 adducts.6c,7
A typical procedure for addition of INO3 to alkenes is as follows:1 to AgNO3 (6.8 g, 0.04 mol) in 50 mL dry CHCl3 and 15 mL anhyd. pyridine is added
dropwise 6.5 g (0.04 mol) ICl in 20 mL CHCl3. AgCl is filtered and washed with CHCl3–pyridine and 0.04 mol of (E)-4,4-dimethyl-2-pentene is added.
After 3 h of stirring, the mixture is poured into ether, filtered, and concentrated to yield 8.7 g (76%) of erythro-3-iodo-4,4-dimethyl-2-pentyl
nitrate and 5% of an iodopyridinium salt.
From: http://onlinelibrary.wiley.com/doi/10.1002/047084289X.ri016/...
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