CHED 361

Search for convenient precursors to hydroxycarbenes

Dasan M. Thamattoor and Sarah Poplawski. Department of Chemistry, Colby College, 5750 Mayflower Hill, Waterville, ME 04901, fax: 207-872-3804,

Although carbene chemistry has enjoyed the attention of numerous researchers, hydroxycarbenes (1) continue to defy detailed study. This is largely due to the lack of suitable general methods for producing these elusive species. To address this long standing problem, we are currently preparing novel precursors (e.g. 2 and 3) which, upon photolysis, could provide an exceptionally facile route to hydroxycarbenes. The design of 2 and 3 is based on the evidence that various other carbenes have been successfully generated from similar systems. In these precursors, extrusion of the carbene is accompanied by the formation of stable aromatic molecules such as phenanthrene and naphthalene. Furthermore, ab initio molecular orbital calculations of hydroxycarbenes, using modern methods and basis sets, will be also described.