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Dual Supermesityl Stabilization: A Room‐Temperature‐Stable 1,2,4‐Triphosphole Radical, Sigmatropic Hydrogen Rearrangements, and Tetraphospholide Anion
Author(s) -
Ionkin Alex S.,
Marshall William J.,
Fish Brian M.,
Marchione Alexander A.,
Howe Laurie A.,
Davidson Fredric,
McEwen Charles N.
Publication year - 2008
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200800265
Subject(s) - chemistry , sigmatropic reaction , caesium , ion , hydrogen bond , hydrogen , aromaticity , medicinal chemistry , inorganic chemistry , organic chemistry , molecule
Cesium 3,5‐bis(2,4,6‐tri‐ tert ‐butylphenyl)‐1,2,4‐triphospholide ( 12 ) and cesium 5‐(2,4,6‐tri‐ tert ‐butylphenyl)tetraphospholide ( 13 ) were synthesized and isolated with flat five‐membered rings, which are an indication of the aromaticity in these anions. Compound 13 is the first example of a stable tetraphospholide anion, which is structurally characterized. Kinetic stabilization of the 1,2,4‐triphospholide system by two supermesityl groups resulted in the detection of the room‐temperature‐stable radical 17 and the observation of a series of successive sigmatropic hydrogen shifts in the first stable 1 H ‐1,2,4‐triphosphole 14 with a P–H bond.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)