Abstract
The importance of the pentavalent state to organic chemistry may readily be seen by considering the broad scope of substitution reactions at carbon, silicon, phosphorus, and related elements. In addition to being involved in the transition state of the SN2 reaction of all these elements, substitution at silicon and phosphorus may also involve pentavalent intermediates. In view of the importance of phosphate ester hydrolyses in life processes, it is not surprising that most of our knowledge of such intermediates is concerned with phosphoranes having two or more P—O bonds. The role of such oxyphosphoranes in phosphate hydrolysis and in particular the effects of phosphorane polytopal rearrangements (vide infra) on the stereochemistry of the overall reaction have been reviewed (R-68,R-70, W-68, UR-72).
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© 1977 Springer-Verlag Berlin Heidelberg
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Kwart, H., King, K. (1977). Pentacovalency. In: d-Orbitals in the Chemistry of Silicon, Phosphorus and Sulfur. Reactivity and Structure Concepts in Organic Chemistry, vol 3. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46342-6_5
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DOI: https://doi.org/10.1007/978-3-642-46342-6_5
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-46344-0
Online ISBN: 978-3-642-46342-6
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