74646-30-3Relevant academic research and scientific papers
Tellurium-Mediated Cycloaromatization of Acyclic Enediynes under Mild Conditions
Landis, Chad A.,Payne, Marcia M.,Eaton, David L.,Anthony, John E.
, p. 1338 - 1339 (2007/10/03)
The cycloaromatization of acyclic enediynes typically requires very high temperatures (>160 °C) and dilute conditions to proceed in a synthetically useful yield. These conditions hinder reaction throughput, inhibiting the use of this reaction for the large-scale production of materials. The reaction of sodium telluride with acyclic arenediynes yields the corresponding tellurepine, which under gentle heating extrudes Te° to yield the cycloaromatization product. We have developed conditions that form sodium telluride from inexpensive tellurium metal in situ, and that also perform the desilylation of silylated arenediynes in the same process. Under our conditions, we are able to perform desilylation and cycloaromatization at temperatures as low as 40 °C and on a scale as large as 5 g in standard laboratory glassware. Copyright
The Bergman reaction as a synthetic tool: Advantages and restrictions
Bowles, Daniel M,Palmer, Grant J,Landis, Chad A,Scott, John L,Anthony, John E
, p. 3753 - 3760 (2007/10/03)
The Bergman cycloaromatization reaction efficiently converts easily prepared acyclic enediynes into aromatic rings. In order to prepare larger, functionalized fused aromatic systems using this reaction, a thorough understanding of how functionalization affects cycloaromatization is necessary. We present here our studies on the influence of substituents at three different functionalization sites on cycloaromatization, and how these functional groups can be tailored to prepare more complex systems.
