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. Author manuscript; available in PMC: 2013 Jun 19.
Published in final edited form as: J Am Chem Soc. 2008 Jan 4;130(4):1440–1452. doi: 10.1021/ja0773507

Table 6.

1,2-Halogen Migration/Cycloisomerization toward Halofurans 21

graphic file with name nihms382578u6.jpg

Entry Substrate Time Product Yield (%)a
1 graphic file with name nihms382578t47.jpg 1 day graphic file with name nihms382578t48.jpg 21b 75
2 graphic file with name nihms382578t49.jpg 1 day graphic file with name nihms382578t50.jpg 21c 73
3 graphic file with name nihms382578t51.jpg 1 hr graphic file with name nihms382578t52.jpg 21d 73
4 graphic file with name nihms382578t53.jpg 1 day graphic file with name nihms382578t54.jpg 21e 61
5 graphic file with name nihms382578t55.jpg 0.5 hr graphic file with name nihms382578t56.jpg 21f 88
6 graphic file with name nihms382578t57.jpg 3 days graphic file with name nihms382578t58.jpg 21g 73
7 graphic file with name nihms382578t59.jpg 5 min graphic file with name nihms382578t60.jpg 21h 97
8b graphic file with name nihms382578t61.jpg 1 hr graphic file with name nihms382578t62.jpg 21i 71
9 graphic file with name nihms382578t63.jpg 3 days graphic file with name nihms382578t64.jpg 21j 48
10b graphic file with name nihms382578t65.jpg 1 hr graphic file with name nihms382578t66.jpg 21k 67c
graphic file with name nihms382578t67.jpg 21l
a

Isolated yields, reactions were performed on 0.29–1 mmol scale with 1 M concentration of 20.

b

Mixture of allene and corresponding propargyl isomer was employed (see Supporting Information).

c

Mixture (2:1) of 21k and 21l by 1H NMR.