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Author: Subject: 2,5-dimethoxy-4-iodo-beta-nitrostyrene
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[*] posted on 15-3-2014 at 03:23

Quote: Originally posted by Methyl.Magic  
Hi, Red-Al causes dehalogenation for sure.

Is that speculation or an experimental result? On what halogens?
Could you please tell us the source of the hyperlab Vitride reduction because the rhodium archive reduction with vitride is claimed to give high yield but in fact did not work at all...

In the "The Khomeinines" thread (topic post #528139) you can find a couple of examples of arylnitropropenes reductions with Red-Al aka Vitride. Here is one example performed by his holiness the ayatollah Khomeini:
3C-Kh3i: 5.42 g (18.4 mmol, MW 295) 3C-Kh3i NP is dissolved in 150 mL toluene (though 100 mL would have been sufficient) and is added drop-wise over a period of 30 min to an ice-cooled stirred mixture of 62 mL 70% vitride (~12 eq) and 50 mL toluene. The ice bath is maintained a further hour when addition is complete and the reaction is allowed to continue overnight. It is subsequently neutralized with 5% aq NaOH and the organic phase is isolated. The latter is washed with 2x 100 mL 5% aq NaOH and 2x 100 mL brine. The organic phase is extracted with 3x 100 mL 10% aq HCl and the combined extracts washed with 75 mL toluene and neutralized with 40% aq NaOH. The neutralized mixture is extracted with 3x 150 mL dichloromethane and the combined organic phases dried over sodium sulfate. After filtration of solids and evaporation of volatiles, 4.33 g of a slightly yellowish oil remains. This is taken up in 75 mL MeOH and neutralized by addition of 4 mL 5 N IPA/HCl. Evaporation of the alcohols gives a crude powder which is recrystallized from CH3CN/IPA, yielding 3.73 g (66.8%, MW 303.5) of a glistering powdery substance, mp 154-155°C.
MS: 267 ([M]+., 0.03%), 44 ([C2H4NH2]+, 100%), 224 ([M-C2H3NH2]+., 5.3%), 182 ([M-C2H3NH2-C3H6]+., 16.3%), 153 ([m/z 182-C2H5]+, 6.4%), 154 ([m/z 182-CO]+, 4.7%)

See also his report in the "3C-E (Vitride reduction)" thread (#521627).

…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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