Communication
ChemComm
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19 (a) V. Strukil, B. Bartolec, T. Portada, I. Ðilovic, I. Halasz and
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21 Full geometry optimization and vibrational calculations were per-
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25 Mechanochemical reactions were carried out using a Retsch MM301
ball mill operating at 30 Hz and in-house manufactured 14 mL
transparent poly(methylmetha)acrylate (PMMA) milling vessels with
two 7 mm diameter stainless steel balls (ball weight 1.3 g). For each
experiment, 266 mg (1.38 mmol) azide and 150 mg (1.38 mmol)
amine were directly weighed to one half of the reaction vessel. The
other half was filled with grinding balls and 75 mL of the liquid
additive giving the same ratio of liquid volume to mass of solid
reactants (Z) in all experiments, Z = 0.18 mL mgÀ1. The two halves of
the jar were carefully joined together so that the solids did not mix
with the liquid before milling was initiated. In situ monitoring was
performed as described before using a portable Raman spectro-
meter13 with a PD-LD LS2 laser source (784 nm). Scattered radiation
was analysed using an Oceanoptics Maya2000 Pro spectrometer.
The Raman probe for the laser was positioned below the milling
vessel for data collection. Each spectrum was typically collected for
10 seconds. The PMMA vessel contribution to the collected Raman
spectra was subtracted. Products were characterized by 1H and 13C
NMR and infrared spectroscopy (Fig. S1–S4 in the ESI†) as well as by
PXRD (Fig. S16 in the ESI†).
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13 (a) D. Gracin, V. Strukil, T. Friscic, I. Halasz and K. Uˇzarevic, Angew.
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Chem., Int. Ed., 2014, 53, 6193; (b) M. Juribasic, K. Uˇzarevic,
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D. Gracin and M. Curic, Chem. Commun., 2014, 50, 10287.
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A. Puskaric, S. A. J. Kimber, P. J. Beldon, A. M. Belenguer, F. Adams,
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V. Honkimaki, R. E. Dinnebier, B. Patel, W. Jones, V. Strukil and
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T. Friscic, Angew. Chem., Int. Ed., 2013, 52, 11538.
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16 S. L. Childs, N. Rodrıguez-Hornedo, L. S. Reddy, A. Jayasankar,
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27 A. Delori, T. Friscic and W. Jones, CrystEngComm, 2012, 14, 2350.
18 That the Curtius rearrangement is possible using this substrate was
verified by heating the solution of acyl azide where isocyanate was
formed.
Also, for a pseudo-fluid model of milling reactions see: X. Ma,
W. Yuan, S. E. J. Bell and S. L. James, Chem. Commun., 2014,
50, 1585.
Chem. Commun.
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