N‐Heterocyclic Carbenes as Promotors for the Rearrangement of Phosphaketenes to Phosphaheteroallenes: A Case Study for OCP to OPC Constitutional Isomerism | Zendy

Li Zhongshu | Zendy; Chen Xiaodan | Zendy; Benkő Zoltán | Zendy; Liu Liu Leo | Zendy; Ruiz David A. | Zendy; Peltier Jesse L. | Zendy; Bertrand Guy | Zendy; Su ChenYong | Zendy; Grützmacher Hansjörg | Zendy

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N‐Heterocyclic Carbenes as Promotors for the Rearrangement of Phosphaketenes to Phosphaheteroallenes: A Case Study for OCP to OPC Constitutional Isomerism

Author(s) -

Li Zhongshu,

Chen Xiaodan,

Benkő Zoltán,

Liu Liu Leo,

Ruiz David A.,

Peltier Jesse L.,

Bertrand Guy,

Su ChenYong,

Grützmacher Hansjörg

Publication year - 2016

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/anie.201600903

Subject(s) - isomerization , chemistry , molecule , structural isomer , stereochemistry , reaction mechanism , medicinal chemistry , catalysis , computational chemistry , organic chemistry

The concept of isomerism is essential to chemistry and allows defining molecules with an identical composition but different connectivity (bonds) between their atoms (constitutional isomers) and/or a different arrangement in space (stereoisomers). The reaction of phosphanyl ketenes, (NHP)−P=C=O (NHP=N‐heterocyclic phosphenium) with N‐heterocyclic carbenes (NHCs) leads to phosphaheteroallenes (NHP)−O−P=C=NHC in which the PCO unit has been isomerized to OPC. Based on the isolation of several intermediates and DFT calculations, a mechanism for this fundamental isomerisation process is proposed.

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