Synthesis, structure, and reactivity of a symmetrically substituted 9-phosphatriptycene oxide and its derivatives

✍ Scribed by Tomohiro Agou; Junji Kobayashi; Takayuki Kawashim

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 167 KB
• Volume: 15
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20038

✦ Synopsis

Abstract

Novel 9‐phosphatriptycenes were synthesized by utilizing ortho‐lithiation of a triarylphosphine oxide as a key step. The structural analysis of the 9‐phosphatriptycene oxide revealed its highly distorted structure around the phosphorus atom, which is consistent with the up‐field shift in the ^31^P NMR spectrum. The 9‐phosphatriptycene and its chalcogenides were synthesized by ordinary methods, and the spectral comparisons of these chalcogenides indicated the large s‐character of the lone‐pair orbital or the phosphorus–chalcogen σ bonds of those species. The 9‐phosphatriptycene oxide was reacted with lithium naphthalenide to give the ring‐opened products. © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:437–446, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20038