Issue 76, 2016

N-Heterocyclic carbene phosphaketene adducts as precursors to carbene–phosphinidene adducts and a rearranged π-system

Abstract

The nucleophilic attack of NHCs on the electron deficient carbon of tetryl substituted phosphaketenes Ph3E–P[double bond, length as m-dash]C[double bond, length as m-dash]O (E = Sn–Si), leads quantitatively to the formation of NHC–phosphaketene adducts. With E = Sn or Ge, these zwitterionic adducts decompose upon thermolysis under the release of carbon monoxide to give zwitterionic NHC–phosphinidene adducts. With E = Si an OCP to CPO rearrangement occurs which leads to the formation of a linear π-conjugated molecule, NHC[double bond, length as m-dash]C[double bond, length as m-dash]P–O–SiPh3.

Graphical abstract: N-Heterocyclic carbene phosphaketene adducts as precursors to carbene–phosphinidene adducts and a rearranged π-system

Supplementary files

Article information

Article type
Communication
Submitted
19 Jul 2016
Accepted
09 Aug 2016
First published
09 Aug 2016

Chem. Commun., 2016,52, 11343-11346

N-Heterocyclic carbene phosphaketene adducts as precursors to carbene–phosphinidene adducts and a rearranged π-system

Z. Li, X. Chen, Y. Li, C. Su and H. Grützmacher, Chem. Commun., 2016, 52, 11343 DOI: 10.1039/C6CC05916C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements