Pentachlorophenyl chloroformate

The reagent is prepared by reaction of pentachlorophenyl chloroformate (m.p. 58°) with /-butanol in benzene in the presence of pyridine. Like /-butyl azidoformate and /-butyl p-nitrophenyl carbonate, it reacts with amino acids to give /-butyloxy-carbonylamino acids in yields of 60-85%. ... 

Methylene chloride-soluble residues. Methylene chloride-or chloroform-soluble C-labeled products were major residues in all of the plant tissues examined except peanut cell ciiltures (Figure 3). Chloroform-soluble C accounted for 59.2 of the radioactivity isolated from peanut roots 48 hr after treatment with [ C]PCNB. The radioactivity was in the form of PCNB (28.7 ), pentachloroaniline (22.5 ), pentachlorothiophenol (2.6 ) pentachlorothloanlsole (3.1 ) pentachlorothloanlsole sulfoxide (0.5 ) S-(pentachlorophenyl)-2-thioaoetic acid [(S-(PCP)ThioAcetate] (0.5 ) and S-(pentachlorophenyl)-3-thio-2-hydroxypropionic acid [S-(PCP)ThioLactate] (0.2 ) and S-(PCP)Cys (trace) (J), The structures of these compounds are shown in Figure 13. Based on TLC, the last three compounds in this list were classified as polar chloroform- or methylene chloride-soluble residues and the remaining compounds were classified as nonpolar residues. 

Vinyl Pentachlorophenyl Ether, (9). Method A 2-Pentachlo-phenoxyethyl bromide (0.4 g, 1.1 mmol) was dissolved In tetrahydrofuran (3 ml) and l,5-dlazablcyclo-5,4,0-undec-5-ene (DBU) (0.16 g, 1.1 mmol) was added dropwlse to the solution. The mixture was refluxed for 30 minutes and water (100 ml) was added, and the solution was extracted with chloroform. The chloroform extract was dried with anhydrous MgS04 and the chloroform removed In vacuo to yield 0.2 g (64.5%) of (9). 

Peptide synthesis, N-protection Acetic-formic anhydride. Adamantyl chloroformate. Benzylthiocarbonyl chloride. /-Butoxycarbonyl-N-hydroxysuccinimide ester. /-Butyl azido-formate. /-Butylcarbonic diethylphosphoric anhydride. /-Butyl fluoroformate. /-Butyl oxycarbonyl fluoride. /-Butyl pentachlorophenyl carbonate. /-Butyl 2,4,5-trichlorophenyl carbonate. Carbobenzoxy chloride. 3,5-Dimethoxybenzyl p-nitrophenyl carbonate. [2-(Diphenyl)isopropyljphenyl carbonate. /-Pentyl chloroformate. 

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