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. Author manuscript; available in PMC: 2016 Sep 16.
Published in final edited form as: European J Org Chem. 2014 Dec 22;2015(4):750–764. doi: 10.1002/ejoc.201403250

Table 2.

Reactions between benzyne and other enol ethers or vinylene carbonate.[a]

Entry Reactant Product Time (h), yield
1 graphic file with name nihms-700515-t0002.jpg graphic file with name nihms-700515-t0003.jpg 2: 2 h, 72%
2 graphic file with name nihms-700515-t0004.jpg graphic file with name nihms-700515-t0005.jpg 3: 6 h, 69%
3 graphic file with name nihms-700515-t0006.jpg graphic file with name nihms-700515-t0007.jpg 4a, 4b: 3 h, 48% 1:1 mixture
4 graphic file with name nihms-700515-t0008.jpg graphic file with name nihms-700515-t0009.jpg 5: 1 h, 50%[b]
5 graphic file with name nihms-700515-t0010.jpg NA[c]
6 graphic file with name nihms-700515-t0011.jpg NA[c] [d]
7 graphic file with name nihms-700515-t0012.jpg graphic file with name nihms-700515-t0013.jpg 6: 2 h, 84%
[a]

Reactions were conducted at a 0.125 m concentration of 2-(trimethylsilyl)phenyl triflate in MeCN, in the presence of 1.2 equiv. of the enol ether (or vinylene carbonate), 2 equiv. of CsF, and 2 equiv. of 18-Cr-6 at room temperature.

[b]

Yield obtained with 3 equiv. of ethyl vinyl ether.

[c]

n.a.: not applicable.

[d]

About 86% of the glycal was recovered.