214628-11-2Relevant academic research and scientific papers
A versatile synthetic route to dehydrobenzoannulenes via in situ generation of reactive alkynes
Bell, Michael L,Chiechi, Ryan C,Johnson, Charles A,Kimball, David B,Matzger, Adam J,Brad Wan,Weakley, Timothy J.R,Haley, Michael M
, p. 3507 - 3520 (2007/10/03)
This paper outlines the development of a protocol that allows in situ generation of unstable alkynes under Pd-catalyzed cross-coupling conditions. Cu-mediated intramolecular cyclization of the resultant α,ω-polyynes provides dehydrobenzoannulenes as singular species, in very good overall yields, and in a variety of topologies that are inaccessible by traditional routes or previously available in low yield only. In addition, we will discuss the solid-state structure and reactivity of these macrocycles, as well as the ability of the planar dehydrobenzoannulenes to support weak induced ring currents.
Synthesis of expanded planar dehydrobenzoannulenes: Weakly diatropic, weakly paratropic, or atropic?
Wan, W. Brad,Kimball, David B.,Haley, Michael M.
, p. 6795 - 6798 (2007/10/03)
Use of a Cu/Pd cross-coupling strategy has led to the synthesis of the first dehydrobenzoannulenes containing triacetylenic linkages. NMR studies of these macrocycles and comparison with other known systems indicate that, in spite of their large size and extensive benzannelation, dehydrobenzoannulenes possess weak induced ring currents.
