Synthesis and characterization of two new triphenylphosphonium halochromates, (C6H5)3PH[CrO3X], (X=F, Br)

Shahriare Ghammamy; Kheyrollah Mehrani; Zahra Javanshir; Ali Moghimi; Fahmideh Shabaani; Saeid Maleki

doi:10.3998/ark.5550190.0008.f07

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Synthesis and characterization of two new triphenylphosphonium halochromates, (C6H5)3PH[CrO3X], (X=F, Br)

Shahriare Ghammamy; Kheyrollah Mehrani; Zahra Javanshir; Ali Moghimi; Fahmideh Shabaani; Saeid Maleki

Volume 2007, Issue 15, pp. 61-65

DOI: http://dx.doi.org/10.3998/ark.5550190.0008.f07

Paper ID: 07-2394AP

Received on 2007-02-21; Accepted on 2007-09-06; Published on 2007-09-21

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General Papers ARKIVOC 2007 (xv) 61-65 Synthesis and characterization of two new triphenylphosphonium halochromates, (C6H5)3PH[CrO3X], (X=F, Br) Shahriare Ghammamy,a,b* Kheyrollah Mehrani,a Zahra Javanshir, a Ali Moghimi,c, Fahmideh Shabaani,a and Saeid Malekia aDepartment of Chemistry, Islamic Azad University, Ardebil Branch, Ardebil, Iran bDepartment of Chemistry, Faculty of Science, Imam Khomeini International University, Ghazvin, Iran c Department of Chemistry, Faculty of Science, Islamic Azad University, Varamin, Iran E-mail: [email protected] or [email protected] Abstract Two new mild oxidizing agents, triphenylphosphonium fluorochromate (TriPPFC), triphenylphosphonium bromochromate (TriPPBC), have been easily prepared. These reagents are suitable for oxidizing various primary and secondary alcohols to their corresponding carbonyl compounds. TriPPFC and TriPPBC have many advantages over similar oxidizing agents including: ease of preparation, involving, simple cationic exchange; high yields of the oxidized species; short reaction times; good selectivity; lower oxidant/substrate ratio and lower solvent requirement. Keywords: Chromium(VI), triphenylphosphonium fluorochromate, triphenylphosphonium bromochromate, oxidation, organic substrate, alcohols Introduction By far the most commonly used method for the synthesis of aldehydes and ketones are the oxidation of alcohols. Many new oxidative methods have been described over the 30 last years. Significant improvements are achieved in the development of new Cr(VI) based oxidizing agents, such as: the Collins reagents,1 chromium trioxide-3,5-dimethylpyrazole complex,2 pyridinium chlorochromate (PCC),3 pyridinium dichromate (PDC),4 2,2'-bipyridinium chlorochromate (BiPCC),5 pyridinium fluorochromate (PFC)6-9 quinolinium fluorochromate,10 quinolinium chlorochromate,11 and 3,5-dimethylpyrazolium fluorochromate (DmpzHFC)12. Industrial demands have led many workers to search for more ideal oxidants with a number of specifications including: lower cost, higher yields, better selectivity, milder neutral conditions, easier preparations, high solubility, less toxicity, and short reaction times. Even though, ISSN 1551-7012 Page 61 ©ARKAT USA, Inc.