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Are terminal aryl butadiynes stable? Synthesis and X-ray crystal structures of a series of aryl- and heteroaryl-butadiynes (Ar-C C-C C-H)

West, K.; Wang, C.S.; Batsanov, A.S.; Bryce, M.R.

Authors

K. West

C.S. Wang



Abstract

The synthesis and isolation are reported of a range of terminal aryl- and heteroaryl-butadiynes (ArC⋮C−C⋮CH) 4a−h from 2-methyl-6-(aryl/heteroaryl)hexa-3,5-diyn-2-ol precursors. The stability of 4a−h in solution is concentration dependent:  many of the derivatives can be stored as dilute solutions for several days or even weeks. The X-ray crystal structures have been obtained for five ArC⋮C−C⋮CH derivatives [Ar = 2-(9-fluorenonyl), 4-biphenyl, 2-pyridyl, 4-pyridyl, and 2-pyrazyl].

Citation

West, K., Wang, C., Batsanov, A., & Bryce, M. (2006). Are terminal aryl butadiynes stable? Synthesis and X-ray crystal structures of a series of aryl- and heteroaryl-butadiynes (Ar-C C-C C-H). Journal of Organic Chemistry, 71(22), 8541-8544. https://doi.org/10.1021/jo0615697

Journal Article Type Article
Publication Date 2006
Journal Journal of Organic Chemistry
Print ISSN 0022-3263
Electronic ISSN 1520-6904
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 71
Issue 22
Pages 8541-8544
DOI https://doi.org/10.1021/jo0615697