Functionalization of Imidazolin-2-imine by Phenyl isocyanate and Chlorodiphenylphosphine- Syntheses and Reactivity Study

Kundu, A (2014) Functionalization of Imidazolin-2-imine by Phenyl isocyanate and Chlorodiphenylphosphine- Syntheses and Reactivity Study. Masters thesis, IIT Hyderabad.

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Abstract

The thesis work describes the functionalization of imidazolin-2-imine (1a, 1b and 1c) on the exocyclic nitrogen (the imine nitrogen) by phenyl isocyanate and chlorodiphenylphosphine. We prepared N-(1,3-di-tert-butylimidazole-2-ylidene)-N’-phenylurea 2a, N-(1,3-dimesitylimidazole-2- ylidene)-N’-phenylurea 2b, N-(1,3-bis-(2,6-diisopropylphenyl)imidazole-2-ylidene)-N’-phenylurea 2c ligands by reacting imidazoline-2-imine with phenyl isocyanate at ambient temperature. To expand imidazolin-2-imine into the novel imidazolin-2-ylidene-1,1-diphenylphosphinamine ligand family we prepared 1,3-dimesitylimidazolin-2-ylidene-1,1-diphenylphosphinamine 3b and 1,3-bis-(2,6- diisopropylphenyl)-imidazolin-2-ylidene-1,1-diphenylphosphinamine 3c ligands by reacting imidazolin-2-imine with chlorodiphenylphosphine in THF:CH2Cl2 mixture at ambient temperature. Further functionalization was done on the imidazolin-2-ylidene-1,1-diphenylphosphinamine by making its chalcogenides. Reaction of 1,3-dimesitylimidazolin-2-ylidene-1,1-diphenylphosphinamine with H2O2, elemental sulphur and selenium affords corresponding oxide, sulphide and selenide derivatives, 1,3-dimesitylimidazolin-2-ylidene-P,P-diphenylphosphinicamide 4b, 1,3- dimesitylimidazolin-2-ylidene-P,P-diphenylphosphinothioicamide 5b and 1,3-dimesitylimidazolin-2- ylidene-P,P-diphenylphosphinoselenoicamide 6b respectively in good yield. Compound 2a, 2b and 2c are introduced in the late transition metal chemistry to prepare nickel complexes (7a and 7b) and to explore its possible application in organic transformation. All the compounds are characterized by spectroscopically such as NMR, IR, UV and solid state structure established by XRD.

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