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The Journal of Organic Chemistry

The Journal of Organic Chemistry

IF: 3.29
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Conversion of Bis(trichloromethyl) Carbonate to Phosgene and Reactivity of Triphosgene, Diphosgene, and Phosgene with Methanol1

Published:8 November 2000 DOI: 10.1021/jo000820u PMID: 11101377
Lucia Pasquato, Giorgio Modena, Livius Cotarca, Pietro Delogu, Silvia Mantovani

Abstract

Triphosgene was decomposed quantitatively to phosgene by chloride ion. The reaction course was monitored by IR spectroscopy (React-IR), showing that diphosgene was an intermediate. The methanolysis of triphosgene in deuterated chloroform, monitored by proton NMR spectroscopy, gave methyl chloroformate and methyl 1,1,1-trichloromethyl carbonate in about a 1:1 ratio, as primary products. The reaction carried out in the presence of large excess of methanol (0.3 M, 30 equiv) was a pseudo-first-order process with a kobs of 1.0 × 10-4 s-1. Under the same conditions, values of kobs of 0.9 × 10-3 s-1 and 1.7 × 10-2 s-1 for the methanolysis of diphosgene and phosgene, respectively, were determined. The experimental data suggest that, under these conditions, the maximum concentration of phosgene during the methanolysis of triphosgene and diphosgene was lower than 1 × 10-5 M. Methyl 1,1,1-trichloromethyl carbonate was synthesized and characterized also by the APCI-MS technique.

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Procduct Name CAS Molecular Formula Supplier Price
Methanol 67-56-1 CH4O 838 suppliers $9.00-$7620.00
Triphosgene 32315-10-9 C3Cl6O3 478 suppliers $10.00-$4341.65
Chloroform-d 865-49-6 CCl3D 221 suppliers $15.00-$1310.00
Diphosgene 503-38-8 C2Cl4O2 132 suppliers $15.00-$1169.94
Tributylmethylammonium methyl carbonate 274257-37-3 C15H33NO3 8 suppliers $251.00-$2991.86
Methyl chloroformate [methyl-14C] ClCOOCH3 1 suppliers Inquiry

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