Imidazole, 4-methyl-, iodination

Imidazole, 4,5-dibromo-l-methyl-synthesis, S, 399 Imidazole, 4,5-di-t-butyl-synthesis, S, 483 X-ray diffraction, S, 350 Imidazole, 4,5-dichloro-chlorination, S, 398 synthesis, S, 398, 473 Imidazole, 4-(3,4-dichlorophenyl)-nitration, 5, 433 Imidazole, 4,5-dicyano-hydrolysis, S, 435-436 synthesis, S, 461, 472, 487 Imidazole, 4,5-dicyano-1-vinyl-synthesis, S, 387 Imidazole, 4,5-dihydro-mass spectra, 5, 360 Imidazole, 4-(dihydroxybutyl)-synthesis, S, 484 Imidazole, 4,5-diiodo-nitration, S, 396 synthesis, S, 400 Imidazole, 2,4-diiodo-5-methyl-iodination, S, 400 Imidazole, 1,2-dimethyl-anions... 

Imidazole, 1 -hydroxy-2,4,5-triphenyl-3-oxides reactions, S, 455 Imidazole, iodo-nitrodehalogenation, 5, 396-397 Imidazole, 1-iodo-reactions, S, 454 stability, S, 110 Imidazole, 2-iodo-synthesis, S, 401 Imidazole, N-iodo-, S, 393 reactions, 5, 454 Imidazole, 4-iodo-5-methyl-iodination, 5, 400 Imidazole, 2-isopropyl-4-nitro-N-nitration, 5, 351 Imidazole, 2-lithio-reactions, S, 106, 448 Imidazole, 2-mercapto-l-methyl-as antithyroid drug, 1, 171 mass spectra, 5, 358 Imidazole, 1-methoxymethyl-acylation, S, 402 Imidazole, 5-methoxy-l-methyl-reactions... 

The use of GSR has been reported to effect deoxygenation of an a-hydroxy ketone.188 Treatment of methyl2,6-di-0-pivaloyl-a-D-ribo-hexopyranosid-3-ulose (147, Scheme 39) with triphenylphosphine, imidazole, and iodine, resulted in deoxygenation to afford methyl 4-deoxy-2,6-di-0-pivaloyl-a-D- ryf/i/w-hexopyranosid-3-ulose (148). Presumably the reaction proceeds via initial formation of the iodo compound, followed by loss of iodine through the enol form, a precedent for which has been reported.189... 

Imidazole, 4-methyl-annular tautomerism, 5, 363 association, 5, 362 boiling point, 5, 362 bromination, 5, 398 deuteration, 5, 417 diazo coupling, 5, 403 hydrogen bonding, S, 350 hydroxymethylation, 5, 404 iodination, 5, 400 kinetics, 5, 401 mass spectra, 5, 358 melting point, 5, 362 methylation, 5, 364 sulfonation, 5, 397 synthesis, 5, 479-480, 482, 484, 489 Imidazole, 5-methyl-annular tautomerism, 5, 363 Imidazole, l-methyl-4-chloro-ethylation, 5, 386 Imidazole, l-methyl-5-chloro-ethylation, 5, 386 nitration, 5, 395... 

Imidazole, 2,4,5-trichloro-1-methyl-chlorination, 5, 398 Imidazole, 2,4,5-trideutero-iodination, 5, 401 Imidazole, 1-trifiuoroacetyl-reactions, 5, 451-452 Imidazole, 2-trifiuoromethyl-hydrolysis, 5, 432 Imidazole, 2,4,5-triiodo-nitration, 5, 396 synthesis, 5, 400 Imidazole, 1,2,4-trimethyl-photolysis, 5, 377 rearrangement, 5, 378 Imidazole, 1,2,5-trimethyl-photochemical rearrangement, 5, 377 rearrangement, 5, 378 Imidazole, 1,4,5-trimethyl-bromination, 5, 399 3-oxide... 

The 1-bromo derivatives were formed in 85-90% yields when 2-methyl (or -phenyl) - 4H - imidazo [ 2,1 - c ] [ 1,4] benzoxa (or - benzthia) zines were treated with bromine or NBS in acetic acid. Iodination with NIS or iodine monochloride occurred at C-I in the imidazole ring in 75-86% yields, but NCS failed to react (92JOC2737). 

A study of the kinetics of iodination of 2- and 4-methylimidazoles also demonstrated base-catalyzed iodination, but whereas imidazole and its 2-methyl derivative were subject also to uncatalyzed iodination, 4-methylimidazole was not. Relative rates for base-catalyzed iodination (imidazole 2-methylimidazole 4-methylimidazole) were 1 34 667. For uncatalyzed... 

A reagent system consisting of triphenylphosphine/imidazole/iodine in toluene has proven useful for the conversion of trans- 1,2-diols (547) into the corresponding alkenes (549 Scheme 120) (79S469). The imidazole probably forms a solvated complex (548) with triphenylphosphine and iodine. Methyl 4,6-O-benzylidene-a-D-glucopyranoside was transformed into 2,3-dideoxyhex-2-enopyranoside in 75% yield. 

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