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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Highly functionalised (γ-azido/γ-fluoro-β-iodo/)vinyl derivatives from phosphorus based allenes or allenoates: IO
Mandala Anitha1, K C Kumara Swamy
1School of Chemistry, University of Hyderabad, Hyderabad 500 046, Telangana, India. kckssc@uohyd.ac.in kckssc@yahoo.com.
Abstract:
Multifunctional γ-azido/γ-fluoro-β-iodo-vinyl phosphine oxides/phosphonates/esters/sulfone were synthesised by iodination followed by azidation/fluorination of phosphorus-based allenes or allenoates (allenyl esters) or a sulphur based allene. Surprisingly, the reaction of (γ,β)-diiodo-vinyl-phosphonate with TBAF [n-Bu4NF] led to the corresponding allenylphosphonate; in contrast, the use of CsF in a similar reaction led to novel γ-diiodo-allenylphosphonate along with the corresponding non-halogenated allenylphosphonate. The combination AgF2/CuBr could be used to obtain the γ-fluoro-β-iodo-vinyl phosphine oxides and related phosphorus-free γ-fluoro-β-iodo-vinyl esters. In many cases, IO halogen to oxygen non-covalent bonding interactions ('halogen bonding') involving the phosphoryl (P[double bond, length as m-dash]O) oxygen, as evidenced by single crystal X-ray crystallography, are also observed.
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