Highly functionalised (γ-azido/γ-fluoro-β-iodo/)vinyl derivatives from phosphorus based allenes or allenoates: I?O halogen bonding interactions

Article abstract of DOI:10.1039/c9ob00715f

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, I?O halogen to oxygen non-covalent bonding interactions ('halogen bonding') involving the phosphoryl (PO) oxygen, as evidenced by single crystal X-ray crystallography, are also observed.

Full text of DOI:10.1039/c9ob00715f

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Takeharu Haino et al.
Solvent-induced emission of organogels based on tris(phenylisoxazolyl)
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DOI: 10.1039/C9OB00715F
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Organic & Biomolecular Chemistry
Page 3 of 12
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DOI: 10.1039/C9OB00715F
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Organic & Biomolecular Chemistry
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DOI: 10.1039/C9OB00715F
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DOI: 10.1039/C9OB00715F
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A/1.(1 B* -*5 .B)+(5 7.,C'-(

Organic & Biomolecular Chemistry
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DOI: 10.1039/C9OB00715F

A/1.(1 B* -*5 .B)+(5 7.,C'-(
Organic & Biomolecular Chemistry
Page 7 of 12
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DOI: 10.1039/C9OB00715F
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Organic & Biomolecular Chemistry
Page 8 of 12
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DOI: 10.1039/C9OB00715F
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A/1.(1 B* -*5 .B)+(5 7.,C'-(

A/1.(1 B* -*5 .B)+(5 7.,C'-(
Organic & Biomolecular Chemistry
Page 9 of 12
View Article Online
DOI: 10.1039/C9OB00715F
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Organic & Biomolecular Chemistry
Page 10 of 12
View Article Online
DOI: 10.1039/C9OB00715F
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A/1.(1 B* -*5 .B)+(5 7.,C'-(
Organic & Biomolecular Chemistry
Page 11 of 12
View Article Online
DOI: 10.1039/C9OB00715F
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A/1.(1 B* -*5 .B)+(5 7.,C'-(
Organic & Biomolecular Chemistry
Page 12 of 12
View Article Online
DOI: 10.1039/C9OB00715F
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