Oxalyl Chloride related reagents

The related compounds bis(2-mothyl-3-indolyl)glyoxal (263) and bis(3-methyl-l-indolyl)glyoxai (264) - have been prepared by the action of oxalyl chloride on the Grignard reagents derived from 2-methylindole and 3-methylindole, respectively, Eis(l-methyl-3-indolyl)-glyoxal (265) was prepared by the action of oxalyl chloride on 1-methyIindole in ether. 

Related Reagents. Dimethyl Sulfoxide-Oxalyl Chloride Oxalyl Chloride-Aluminum Chloride. 

Related Reagents. 7V-Bromosuccinimide Chloramine-T 7V-Chlorosuccinimide N-(l, 1-Dimethylethyl)benzenesulfinimi-doyl Chloride Tetrapropylammonium Perruthenate Dimethyl sulfoxide-oxalyl Chloride l,l,l-Triacetoxy-l,l-dihydro-l,2-benziodoxol-3(l/7)-one 2-Iodoxybenzoic Acid (IBX) Diphenyl Sulfoxide. 

Related Reagents. Dimethyl Sulfoxide-Acetic Anhydride Dimethyl Sulfoxide-Dicyclohexylcarbodiimide Dimethyl Sulfoxide-Methanesulfonic Anhydride Dimethyl Sulfoxide-Oxalyl Chloride Dimethyl Sulfoxide-Phosgene Dimethyl Sulfoxide-Phosphorus Pentoxide Dimethyl Sulfoxide-Sulfur Trioxide/Pyridine Dimethyl Sulfoxide-Tiifluoroacetic Anhydride Dimethyl Sulfoxide-Triphosgene. 

Related Reagents. A/-Chlorosuccinimide-Dimethyl Sulfide Chromic Acid Dimethyl Sulfide-Chlorine Dimethyl Sulfoxide-Acetic Anhydride Dimethyl Sulfoxide-Dicyclo-hexylcarbodiimide Dimethyl Sulfoxide-Oxalyl Chloride Dimethyl Sulfoxide-Phosphorus Pentoxide Dimethyl Sulfoxide-Sulfur Trioxide/Pyridine Dimethyl Sulfoxide-Trifluoroacetic Anhydride Dimethyl Sulfoxide-Triphosgene Manganese Dioxide Pyridinium Chlorochromate Pyridinium Dichromate Ruthenium(rV) Oxide Silver(I) Carbonate on Celite 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3( 1 H)-ons. 

Oxysulphonium Ylides.—Reagents that are related to DMSO are now in routine use for the selective oxidation of alcohols to aldehydes and ketones. The particularly effective combination of DMSO and oxalyl chloride followed by triethylamine has been shown to involve the intermediacy of a chlorodimethylsulphonium salt (21). ... 

Mancuso, A. J. Swern, D. Activated Dimethyl Sulfoxide Useful Reagents for Synthesis Synthesis 1981,165-185. Mancuso, A. J. Brownfain, D. S. Swern, D. Structure of the Dimethyl Sulfoxide-Oxalyl Chloride Reaction Product. Oxidation of Heteroaromatic and Diverse Alcohols to Carbonyl Compounds /. Org. Chem. 1979, 44, 4148-4150. Mancuso, A. J. Huang, S-L. Swern, E. Oxidation of Long-Chain and Related Alcohols to Carbonyls by Dimethyl Sulfoxide Activated by Oxalyl Chloride J. Org. Chem. 1978, 45, 2480-2482. Omura, K. Swern, D. Oxidation of Alcohols by Activated Dimethyl Sulfoxide. A Preparative Steric and Mechanistic Study Tetrahedron 1978, 54, 1651-1660. 

In order to avoid the need for DCC, a number of activated derivatives of IV-hydroxysuccinimide itself have been developed which react directly with, for example, an oi-amino acid to provide the required activated oi-amino acid esters. These include the commercially available carbonate (1), a stable crystalline solid obtained from HOSu and Trichloromethyl Chloroformate or from 0-trimethylsilyloxysuccinimide and Phosgene and the related phosphate (2) derived from HOSu and Diphenyl Phosphorochlo-ridate under Schotten-Baumann conditions. Another alternative (also commercially available) is the oxalate (3), formed from HOSu and Oxalyl Chloride In general, these intermediates react rapidly with an iV -protected a-amino acid, usually in the presence of a mild base such as pyridine, to provide excellent yields of the required hydroxysuccinimide esters, generally with less racemization than is sometimes associated with the HOSu-DCC method. It is also possible to cany out the entire process of peptide synthesis in one pot using these reagents. 

Related Reagents. Dimethylchloromethyleneammonium Chloride Oxalyl Chloride Phosphorus(III) Chloride Phos-phorus(V) Oxide Phosphorus Oxychloride Thionyl Chloride Triphenylphosphine-Carbon Tetrachloride Triphenylphosphine Dichloride. 

---