Methanes diiodomethane

OICHLORO-METHANE CHLOROFLUORO-METHANE DIFLUORO-METHANE DIIODOMETHANE FORMALDEHYDE FORMIC-ACID BROMOMETHANE CHLOROMETHANE FLUOROMETHANE IODOMETHANE NITROMETHANE METHYL-NITRfTE METHYL-NITRATE METHANE METHANOL METHANETHIOL METHYLAMINE TETRA... 

Eisch and Piotrowski reported the preparation of gem-dizinc compounds from diiodomethane and zinc powder in the titanocene chloride mediated methylenation of ketones in 1983 (equation 5)7. In this case, it was not mentioned that they had used pyrometallurgy zinc. The Tebbe-type reagent 2 was shown as an intermediary species. Before addition of titanocene chloride, the amount of methane was measured after hydrolysis of the reaction mixture to determine the formation of gem-dizinc species7. 

In 1998, Matsubara, Utimoto and coworkers reported a general procedure for the preparation of bis(iodozincio)methane, which was obtained as a THF solution (equation 6)9. The detailed structural study of the solution by SANS (small angle neutron scattering), AXS (anomalous X-ray scattering) and EXAFS (extended X-ray absorption fine structure) implied that the g< wt-dizinc species prepared from diiodomethane and zinc is the monomeric bis(iodozincio)methane (3). Formation of polymethylene zinc 4 via Schlenk... 

The reaction of sodium 4-ethoxybenzenetellurolate with dichloromethane gave products of indefinite composition. However, the reactions of lithium 2-benzothiophenetellurolate with dichloromethane and lithium benzenetellurolate with diiodomethane yielded his[aryltelluro]methane, and those of lithium ethynetellurolates with equimolar amounts of chloroiodomethane gave chloromethyl ethynyl tellurium compounds. v/c-Dibromides and sodium 4-ethoxybenzenetellurolate reacted to produce ethenes and bis[4-ethoxyphenyl] ditellurium. ... 

Bis[4-ethoxyphenyltelluro]methane was also isolated as the dibromomethane adduct (m.p. 154°) or as the diiodomethane adduct (m.p. 118°) from reaction mixtures consisting of the arenetellurolate, the dihalomethane and ethanol/benzene/aqueous sodium hydroxide . Reactions with dichloromethane gave products of indefinite composition . 

Reactions of halogen-stabilized carbenoids with imines have been carried out using prefoimed lithium species (e.g. equation 36), or via a carbenoid generated from diiodomethane utilizing zinc-copper couple (Simmons-Smith conditions). A stereospecific ring closure is observed after the addition of lithiodichloromethane to a benzaldimine (equation 37).The addition of lithiochloro(phenylsulfon-yl)methane to aromatic imines affords 2-phenylsulfonyl-substituted aziridines, which can be deproton-ated and alkylated in excellent yield (Scheme 20). 

In contrast to the reaction with diazomethane, the cyclopropanation of cyclopropylidene(di-spiro[2.0.2.1]heptylidene)methane (15) with diiodomethane/diethylzinc took place predominantly at the reactive central double bond. The product of double cyclopropanation was also obtained in good yield. 

Diiodomethane Dijodmethan EINECS 200-841-5 Methane, diiodo- Methylene diiodide Methylene iodide Methylenjodid Mi-Gee NSC 35804. Used to separate mixtures of minerals, in determination of specific gravity and in the manufacture of x-ray contrast materiais. Liquid mp = 6.1° bp = 182° d ° = 3.3212 soluble in H2O (14 g/1), more soluble in organic solvents. Sigma-Aldrich Fine Chem. U.S. BioChem. 

Essentially all the simple geminal di- or poly halides studied have been derivatives of methane. Reaction of diiodomethane (25,103) with triethyl phosphite proceeds normally, to furnish tetraethyl methanedi-phosphonate and iodomethanephosphonate. However, the reaction between carbon tetrachloride and trialkyl phosphite, first investigated by Kamai and Egorova (156,181), is catalyzed by peroxides or ultraviolet light, and accordingly it has been formulated by Kamai and Kharrasova (157) as a radical-chain process. 

Various Brunauer-Emmett-Teller (BET) surface areas have been obtained for hyper-crosslinked networks of polypyrrole using diiodomethane, triiodo-methane and triiodoborane by erosslinking with CH2, CH and B erosslinkers, respectively. It was also observed that HCPs reduced with metal partieles like Li possess inereased selectivity towards CO2 over CH4, although there was a decrease in surface area as metal partieles fill the pores (not post-synthesis). 

Recently published work [141] showed that the less reactive dibromo-methane could be used for cyclopropanation although the prior activation of the zinc was necessary. The reaction has a long induction period and yields are somewhat lower than those reported using diiodomethane. 

Catechols likewise undergo 0-alkylation under phase transfer conditions, yielding methylenedioxy derivatives on reaction with methylene bromide [8]. This reaction constitutes a useful route to this commonly occurring oxygen heterocycle as well as providing a facile protection method for 1,2-dihydroxyarenes. Dibromo-methane rather than the more reactive diiodomethane was used in this reaction because the latter is a source of iodide ion which poisons the phase transfer catalyst by selectively ion-pairing with the quaternary ammonium cation. Phenoxide ion can apparently compete successfully with bromide but not iodide in the formation of an extractable ion pair under these conditions. 

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