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Triphenylphosphonioacetylide: A Species Isoelectronic with Isocyanides
Author(s) -
Bestmann Hans Jürgen,
Frank Wilhelm,
Moll Claus,
Pohlschmidt Andreas,
Clark Timothy,
Göller Andreas
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980216)37:3<338::aid-anie338>3.0.co;2-5
Subject(s) - chemistry , lewis acids and bases , spectral line , computational chemistry , charge (physics) , crystallography , nmr spectra database , organic chemistry , catalysis , physics , quantum mechanics , astronomy
Stabilized only by triphenylphosphane , the title compound 1 was synthesized and investigated theoretically (the HOMO of 1 is depicted on the right). Both calculations and experimental NMR spectra show that no Lewis structure can describe the geometry and charge distribution accurately. Compound 1 undergoes an equivalent of the Passerini reaction. Ph 3 P + −C≡C − : 1