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. Author manuscript; available in PMC: 2012 Aug 22.
Published in final edited form as: Chemistry. 2011 Jul 27;17(35):9595–9598. doi: 10.1002/chem.201100768

Table 2.

In Situ Intramolecular Schmidt Reaction of New Substrates[a]

Entry Halide Product Yield
(%)
Recovery (%)

(Azide/Halide)
graphic file with name nihms381643t9.jpg graphic file with name nihms381643t10.jpg
1 10a X = Cl 11 51 –/14
2 10b X = Br 11 53
graphic file with name nihms381643t11.jpg graphic file with name nihms381643t12.jpg
3 12a X = Cl 13 77[b] –/11
4 12b X = Br 13 61[b]
5 graphic file with name nihms381643t13.jpg graphic file with name nihms381643t14.jpg 54
6 graphic file with name nihms381643t15.jpg graphic file with name nihms381643t16.jpg 83
7 graphic file with name nihms381643t17.jpg graphic file with name nihms381643t18.jpg trace 66/–
8 graphic file with name nihms381643t19.jpg graphic file with name nihms381643t20.jpg 67
9 graphic file with name nihms381643t21.jpg graphic file with name nihms381643t22.jpg 40

(23:24 = 3:1)
33/–
[a]

Conditions: 1. Substrate 2M in CH3CN, 1.1 equiv. NBu4N3, 300 W MWI, 50 µL/min. 2. TFA (3 mL, excess) 50 µL/min, 40 PSI back pressure.

[b]

Reaction was performed at 125 W.