To link to full-text access for this article, visit this link: http://dx.doi.org/10.1016/j.jorganchem.2010.07.029 Byline: JoA'l Poisson, Ivor Wharf, D. Scott Bohle, Mirela M. Barsan, Yuxuan Gu, Ian S. Butler Abbreviations: Ind, C.sub.8H.sub.6N; Pyr, C.sub.4H.sub.4N Abstract: The biologically important heterocycles pyrrole, C.sub.4H.sub.4N, and indole, C.sub.8H.sub.6N, ought to be useful as reagents in organic synthesis. Unfortunately, working with them has proved to be difficult because they tend to self-polymerize in solution, especially in the presence of acid catalysts. When the self-polymerization can be controlled, however, the pyrrole and indole units should provide an important route to selective N-metal binding, particularly when these ligands are activated by alkyl-lithium reagents. Using this approach, a general synthesis of the group 14 pyrrolides and indolides, Ph.sub.3MX (M=Si, Ge, Sn; X=C.sub.4H.sub.4N, C.sub.8H.sub.6N), has been developed and the results are reported here. The compounds are formed as high-melting, white crystalline solids and have been characterized by.sup.13C-,.sup.29Si- and.sup.119Sn-NMR, Raman and electron-impact mass spectroscopy as well as elemental analysis. A single-crystal X-ray study of Ph.sub.3Si(C.sub.4H.sub.4N) has shown that the compound is disordered in the tetragonal lattice, even at low temperature (100K). Author Affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, Canada H3A 2K6 Article History: Received 17 May 2010; Revised 28 July 2010; Accepted 29 July 2010 Article Note: (footnote) [star] Presented, in part, at the 92nd Canadian Chemistry Conference and Exhibition, Hamilton, Ontario, Canada, May-June 2009.