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Issue 28, 2008
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Promotion of phosphaalkyne cyclooligomerisation by a Sb(v) to Sb(iii)redox process

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A high yield of the tetraphosphaladderene, anti-tetraphosphatricyclo[,5]octa-3,7-diene, is obtained from reaction of the zirconocene 1,3-diphosphabicyclo[1.1.0]butane with Ph2SbCl3 in THF or CH2Cl2. Exploration of the reaction pathway using density functional theory suggests that an envelope-type adduct of Ph2SbCl and 1,3-diphosphabicyclo[1.1.0]butane plays a pivotal role in the reaction. The zwitterionic character of this intermediate species allows it to act simultaneously as both an ene and an eneophile, and a symmetry-allowed bimolecular reaction leads to the tetraphosphaladderene species via a spirocyclic intermediate.

Graphical abstract: Promotion of phosphaalkyne cyclooligomerisation by a Sb(v) to Sb(iii) redox process

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Article information

14 Mar 2008
06 May 2008
First published
12 Jun 2008

Dalton Trans., 2008, 3753-3758
Article type

Promotion of phosphaalkyne cyclooligomerisation by a Sb(V) to Sb(III) redox process

C. Fish, M. Green, R. J. Kilby, J. E. McGrady, D. A. Pantazis and C. A. Russell, Dalton Trans., 2008, 3753
DOI: 10.1039/B804401E

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