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. Author manuscript; available in PMC: 2014 Mar 12.
Published in final edited form as: European J Org Chem. 2010 Jan;2010(3):391–409. doi: 10.1002/ejoc.200901094

Table 2.

graphic file with name nihms-465354-t0036.jpg

entry internal
alkyne
terminal
alkyne
yield a rrb major regioisomer
1 graphic file with name nihms-465354-t0037.jpg 36 60 17:1 graphic file with name nihms-465354-t0038.jpg
2 graphic file with name nihms-465354-t0039.jpg 36 57 ≥ 20:1 graphic file with name nihms-465354-t0040.jpg
3 graphic file with name nihms-465354-t0041.jpg 36 47 ≥ 20:1 graphic file with name nihms-465354-t0042.jpg
4 graphic file with name nihms-465354-t0043.jpg 36 53 ≥ 20:1 graphic file with name nihms-465354-t0044.jpg
5 graphic file with name nihms-465354-t0045.jpg ent-36 64 ≥ 20:1 graphic file with name nihms-465354-t0046.jpg
6 graphic file with name nihms-465354-t0047.jpg ent-36 63 ≥ 20:1 graphic file with name nihms-465354-t0048.jpg
7 graphic file with name nihms-465354-t0049.jpg ent-36 64 ≥ 20:1 graphic file with name nihms-465354-t0050.jpg
8 graphic file with name nihms-465354-t0051.jpg ent-36 68 ≥ 20:1 graphic file with name nihms-465354-t0052.jpg
9 graphic file with name nihms-465354-t0053.jpg 36 78 10:1 graphic file with name nihms-465354-t0054.jpg
a

Yield based on terminal alkyne

b

Regioisomeric ratio with respect to functionalization of the internal alkyne (A/B – defined in Table 1). In a few cases, observable quantities of the minor regioisomer “C” were observed (entry 4 = 12:1, entry 6 = 14:1, entry 7 = 17:1).