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.
|Number of pages||2|
|Journal||Journal of the American Chemical Society|
|State||Published - Feb 11 2004|
Bibliographical noteFunding Information:
I wish to thank Drs. J. Morris Weinberg and T. Hirschfeld for inviting me to present this work at the 20th Annual Symposium on Optical, Electro-optical, Laser and Photographic Technology (sponsored by the Society of Photo-Optical Instrumentation Engineers, SPIE) in August of 1976. I should point out that it was the work of T. E. Orlowski and D. R. Dawson of this laboratory which raised the issues discussed in this paper. I would also like to thank Kevin Jones for many hours of stimulating discussions.
* This work was supported in part by the Sloan Fund. ** Contribution No. 5427. t By right-angle we mean the emission perpendicular to the propagation of the laser beam.
ASJC Scopus subject areas
- Chemistry (all)
- Colloid and Surface Chemistry