Clorodifluoroacetyl Azide, ClF2CC(O)N3: Preparation and Properties

LUIS A. RAMOS; XIAOQING ZENG; SONIA E. ULIC; HELMUT BECKERS; HELGE WILLNER; CARLOS O. DELLA VÉDOVA

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; Año: 2012

0022-3263

 Chlorodifluoroacetyl azide, ClF2CC(O)N3, was prepared and characterized by IR (gas, Ar matrix), Raman (liquid), UV−vis (gas), and 19F, 13C NMR spectroscopy. The vibrational spectra were analyzed in  terms of a single conformer, gauche-syn, where the Cl−C and the NαNβ  bonds are gauche and syn to the CO bond, respectively. The photo and thermal decomposition reactions of the azide were studied with the aid of  matrix isolation. In both cases, a new isocyanate species ClF2CNCO was  produced and characterized by matrix IR spectroscopy. The conforma-  tional properties and the Curtius rearrangement pathways of this new  carbonyl azide were theoretically explored, which suggest the preference  of a concerted over stepwise decomposition for the global minimum  gauche-syn conformer.