Catechol phosphorus trichloride

Dehydration is a process for which many phosgene competitors have proved useful. Thionyl chloride, phosphorus pentoxide, phosphorus oxychloride, triphe-nylphosphine/tetrachloromethane, and catechol phosphorus trichloride are the reagents of choice in many dehydration processes. 

Corey and J. E. Anderson154 have described a useful method for the conversion of alcohols into iodides by employing the reagent 120, which is readily prepared from catechol and phosphorus trichloride. Reaction of 120 in ether solution with an alcohol in the presence of pyridine affords the corresponding phosphite 121. Treat-... 

It has recently been found that the bis-spirophosphorane (182) (easily available from catechol and phosphorus trichloride) undergoes addition of a peptide carboxylate giving the reactive intermediate (183) which can be further reacted with O- protected amino acid salts to produce a new peptide (for example the tripeptide 184) with very little (0.1%) racemization (Scheme 29) (82CC298). 

Platinum(II)15 and palladium(II)16 complexes of phosphorus trichloride undergo solvolysis in water and alcohols to form complexes with orthophosphorous acid or orthophosphite ligands (equation 6). Similar reactions occur between the palladium(II) phenyldichlorophosphine complex (8) and the diols ethyleneglycol and catechol, but new chelate rings are not formed (Scheme 2). Solvolysis also occurs with attack of diphenylphosphinic acid or a similar diphenylchlorophosphine complex (9) (equation 7). The palladium complexes (8) and (9) are unstable to excess methanol, water or base and undergo reduction. Similarly, the phosphorus trichloride gold(I) complex (10) is reduced by water, but forms stable products on reaction with alcohols (equation 8).15 During the above reactions, the phosphorus—metal bond remains intact and the overall process is one of substitution at phosphorus. 

Prepared from catechol and phosphorus trichloride via o-phenylenephosphoro-chloridite. Used in peptide synthesis for the direct interaction of the two com-ponents (compare tetraethyl pyrophosphite). Synthesis of dipeptides is satisfactory, but extensive racemization occurs when N-acyl peptides are employed. 

Catechol, 47, 60, 120, 128, 451, 467-A68, 837, 857, 1011-1012 carbonate, 119-120 dibenzenesulfonate, 47 dichloromethylene ether, 119-120 Catechyl phosphorus trichloride, 120 Cathyl chloride (Ethyl chloroformate), 86, 239, 363, 364-367 Cedrol.913 Cdite, 120 Cellobiose, 893 o-Cellobiose oclaacetate, 158 Cfmulsol, 820 o-Cephalins, 847 Ceric acetate, 1062 Ceric ammonium nitrate, 120-121 Cerous chloride, 121 Cerous hydroxide, 121 Cesium fluoride, 117,121, 933 Cetyl alcohol, 497, 862 Cetyl iodide, 497, 862, 1279 Cetyltrimethylamroonium horohydride, 1143 Cetyltrimelhylaromonium bromide, 121-122 Cevadine, 798 Ovine, 59... 

Carbon suboxide, 52 Carbonylation, 148, 149, 216 Carbonyl chlorofluoride, 48, 54 Carbonyl cyanide, 60-61 N,N -Carbonyldiimidazole, 61 1,1-Carbonyldi-l,2,4-triazole, 61 N-Carbonylsulfamic acid chloride (N-Carbonylsulfamyl chloride), 61 Carboxamides, 270 Carboxamine-N-sulfochlorides, 70 p-Carboxybenzenediazonium chloride, 62 p-Carboxybenzenesulfonazide, 62 Carboxylation, 15, 16 Carboxylic acid anhydrides, 133 Carboxylic acid N,N-dimethylamines, 153 Carboxylic anhydrides, 409-410 p-Carboxyphenylhydrazones, 62 Cardenolides, 130, 131 (S-Carotene, 19 /-Carvone, 451, 452 i//-Caryophyllene, 149, 150 Catechol, 65, 233 Catechol amines, 159 Catechyl phosphorus tribromide, 63 Catechyl phosphorus trichloride, 63 Cis-Cecropia juvenile hormone, 261 Cedrene, 234, 235 a-Cedrene, 349 /3-Cedrene, 349 Cendranoxide, 234, 235 Cephalosporin C, 48 Ceric ammonium nitrate, 63-65 Ceric sulfate. 65 Cesium fluoride, 346 trans-Chalcone oxide, 422 Chalcone phenylhydrazones, 257, 258 Chalcones, 406 Chloramine, 65-66, 69 Chloranil, 66-67, 113, 116, 401,454... 

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