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Tests on an accelerating rate calorimeter (ARC) showed the onset of decomposition at 130  C, with DHdec ¼ 278 J gÀ1 , and a final temperature of 179  C. 2 Phosgene ‘‘Oligomers’’ below the boiling point, although there is no evidence of its decomposition below 130  C [16]. To identify the gases produced from the decomposition of triphosgene, an experiment was performed on a thermogravimetric analyzer interfaced to a Fourier transform infrared spectrometer (TGA-FTIR) [16]. The simultaneous presence of phosgene, diphosgene, carbon dioxide, and tetrachloromethane among the thermal decomposition products suggested another decomposition mechanism, which would be favored by a six-membered transition state, as shown below.

01 mol) was condensed at À50  C. 5 h. The reaction mixture was stirred for a further 12 h at 0  C (ice bath), with monitoring of the reaction by TLC. Thereafter, the cooling bath was replaced by an oil bath and the flask was fitted with a distillation apparatus. 03 Torr). Analyses (1 H and 13 C NMR, IR, TLC) were indicative of a pure product (free from benzyl chloride). Important: During the course of the distillation, the temperature of the oil bath must be kept below 65  C! At higher temperatures, benzyl chloride will be increasingly generated.

J. Davis, Org. Lett. 1999, 1, 933–936. F. : P. T. Anastas, P. Tundo), Oxford 117 118 119 120 121 University Press USA (OUP USA), New York, 2000, p. 201. F. Rivetti, C. R. Acad. Sci. Paris, Se´rie IIc, Chem. 2000, 3, 497–503. F. Rivetti, U. Romano, D. Delledonne, in Green Chemistry: Designing Chemistry for the Environment, ACS Symp. Ser. 626, American Chemical Society, Washington DC, 1996, p. 70. U. Romano, R. Tesei, M. Massi Mauri, P. Rebora, Ind. Eng. Chem. Prod. Res. Dev. 1980, 19, 396–402. N.

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