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. Author manuscript; available in PMC: 2013 Dec 21.
Published in final edited form as: Angew Chem Int Ed Engl. 2012 Nov 19;51(52):13054–13057. doi: 10.1002/anie.201207820

Table 1.

Ring expansion of various 1-sulfonyl 4-tertiary alcohol triazoles 3 yielding products 5. General reaction conditions: 1-sulfonyl triazole (1.0 mmol, 1.0 equiv.), rhodium(II) octanoate (0.5 mol%), CHCl3 (2.0 mL), 70 °C, mw, 5 – 60 min. All values shown represent isolated yields.

Entry Triazole [°C/min] Product Yield
graphic file with name nihms456122t1.jpg graphic file with name nihms456122t2.jpg
1 3a: n = 1 70/15 5a: n = 1 91%
2 3b: n = 2 70/15 5b: n = 2 93%
3 3c: n = 3 70/15 5c: n = 3 94%
graphic file with name nihms456122t3.jpg graphic file with name nihms456122t4.jpg
4 3d: R = p-OMePh 70/60 5d: R = p-OMePh 95%
5 3e: R = p-IPh 70/5 5e: R = p-IPh 71%
6 3f: R = iPr 70/20 5f: R = iPr 66%
7 graphic file with name nihms456122t5.jpg
3g
70/30 graphic file with name nihms456122t6.jpg
5g
92%
8 graphic file with name nihms456122t7.jpg
3h
70/45 graphic file with name nihms456122t8.jpg
5h
98%
9 graphic file with name nihms456122t9.jpg
3i
70/60 graphic file with name nihms456122t10.jpg
5i
89%
10 graphic file with name nihms456122t11.jpg
3j
70/30 graphic file with name nihms456122t12.jpg
5j
95%