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.

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].

• 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
• Public URL: https://durham-repository.worktribe.com/output/1541640