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Phospha‐alkenes and Phospha‐alkynes, Genesis and Properties of the (p‐p)π‐Multiple Bond
Author(s) -
Appel Rolf,
Knoll Fritz,
Ruppert Ingo
Publication year - 1981
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198107311
Subject(s) - pericyclic reaction , alkyne , alkene , ylide , double bond , phosphorus , chemistry , medicinal chemistry , triple bond , carbanion , wittig reaction , nitrogen , organic chemistry , catalysis
Just as the octet rule had prevented the discovery of the inert‐gas compounds, the systematic search for phosphorus‐carbon‐ and phosphorus‐nitrogen‐compounds having (p‐p)π‐multiple bonds was hindered by the double bond rule. The first successful synthesis of mesomeric‐stabilized phosphorus‐carbon compounds with coordination number 2, seventeen years ago, was followed nine years later by the preparation of the imino‐phosphanes whose intensive investigation has continued to the present day. A dramatic development has now begun in the phospha‐alkene and ‐alkyne fields, and a large variety of preparative methods have been found. Several compounds of this type are amazingly stable, however they do not participate in typical ylide reactions such as the Wittig reaction. In contrast, the PC double bond is more comparable to that of olefins, which has been confirmed by the occurrence of E,Z ‐isomers and pericyclic reactions of phospha‐l,5‐hexadienes.