Open AccessSynthesis, structure, and reactivity of a symmetrically substituted 9‐phosphatriptycene oxide and its derivatives
Author(s) -
Agou Tomohiro,
Kobayashi Junji,
Kawashim Takayuki
Publication year - 2004
Publication title -
heteroatom chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.283
H-Index - 42
eISSN - 1098-1071
pISSN - 1042-7163
DOI - 10.1002/hc.20038
Subject(s) - chemistry , heteroatom , chalcogen , lone pair , oxide , lithium (medication) , reactivity (psychology) , ring (chemistry) , lithium atom , atom (system on chip) , phosphine oxide , crystallography , phosphorus , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , molecule , phosphine , catalysis , ion , medicine , alternative medicine , pathology , ionization , computer science , embedded system , endocrinology
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