Synthesis, Crystal Structure and Reactivity Study of N-Pyrrolyl-P, P-Diphenylphosphino Sulfide/Selenide Ligand

Authors

  • Tarun K. Panda Department of Chemistry, Indian Institute of Technology, Hyderabad, Ordnance Factory Estate, Yeddumailaram, Telangana, India
  • Srinivas Anga Department of Chemistry, Indian Institute of Technology, Hyderabad, Ordnance Factory Estate, Yeddumailaram, Telangana, India
  • Tigmansu Pal Department of Chemistry, Indian Institute of Technology, Hyderabad, Ordnance Factory Estate, Yeddumailaram, Telangana, India

DOI:

https://doi.org/10.37591/jomcct.v5i3.2012

Keywords:

Phosphin-imin-methandiides, heteroditopic, phosphinamines, dichloromethane

Abstract

We report the synthesis and solid state structures of the N-pyrrolyl-P,P-diphenylphosphino sulfide and selenide of molecular formulae [C4H4NP(S)Ph2] (1) and [C4H4NP(Se)Ph2] (2) respectively. Compounds 1 and 2 were prepared by one pot reaction of pyrrole and [Ph2P(E)Cl] (E = S and Se) in the presence of NaH as base at ambient temperature. In the solid state structure established by single crystal X-ray diffraction analysis, phosphorus atom adopts a distorted tetrahedral geometry and slight shortening of the P-N bond is observed. The compound 1 was treated with various bases (nBuLi, MeLi, KCH2Ph) to carry out the phospho-Fries rearrangement; however a N-P bond cleavage was observed to yield a sulfur derivative of phosphoalkanes in each case [C4H9P(S)Ph2 (3a), CH3P(S)Ph2 (3b) and PhCH2P(S)Ph2 (3c)]. All the products 3a-c were characterized by 1H and 31P{1H} NMR spectroscopy

Author Biography

Tarun K. Panda, Department of Chemistry, Indian Institute of Technology, Hyderabad, Ordnance Factory Estate, Yeddumailaram, Telangana, India

Indian Institute of Technology
Hyderabad

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Published

2019-05-02

Issue

Vol. 5 No. 3 (2014)

Section

Articles

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