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

被引：11

作者：

Anitha, Mandala ^{[1
]}

Swamy, K. C. Kumara ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 23期

关键词：

PALLADIUM-CATALYZED REACTIONS; STEREOSELECTIVE-SYNTHESIS; ALLENYLPHOSPHONATES/ALLENYLPHOSPHINE OXIDES; PHENYL SULFOXIDES; PHOSPHINE OXIDES; CYCLIZATION; BENZOFURANS; REACTIVITY; REGIO; ACIDS;

D O I：

10.1039/c9ob00715f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Multifunctional gamma-azido/gamma-fluoro-beta-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 (gamma,beta)-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 gamma-diiodo-allenylphosphonate along with the corresponding non-halogenated allenylphosphonate. The combination AgF2/CuBr could be used to obtain the gamma-fluoro-beta-iodo-vinyl phosphine oxides and related phosphorus-free gamma-fluoro-beta-iodo-vinyl esters. In many cases, IO halogen to oxygen non-covalent bonding interactions (halogen bonding') involving the phosphoryl (P?O) oxygen, as evidenced by single crystal X-ray crystallography, are also observed.

引用

页码：5736 / 5748

页数：13

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