Phosphorus-Containing Bis-allenes: Synthesis and Heterocyclization Reactions Mediated by Iodine or Copper Dibromide.

Title Phosphorus-Containing Bis-allenes: Synthesis and Heterocyclization Reactions Mediated by Iodine or Copper Dibromide.
Authors I. Essid; C. Laborde; F. Legros; N. Sevrain; S. Touil; M. Rolland; T. Ayad; J.N. Volle; J.L. Pirat; D. Virieux
Journal Org Lett
DOI 10.1021/acs.orglett.7b00648
Abstract

Bisphosphorylallenes were easily obtained in multigram scale from the Wittig-type rearrangement of bispropargyl alcohols. Unlike other conjugated bis-allenes, these reagents underwent a double cyclization mediated by iodine or copper dibromide leading to the formation of bis-1,2-oxaphospholenes.

Citation I. Essid; C. Laborde; F. Legros; N. Sevrain; S. Touil; M. Rolland; T. Ayad; J.N. Volle; J.L. Pirat; D. Virieux.Phosphorus-Containing Bis-allenes: Synthesis and Heterocyclization Reactions Mediated by Iodine or Copper Dibromide.. Org Lett. 2017;19(7):18821885. doi:10.1021/acs.orglett.7b00648

Related Elements

Iodine

See more Iodine products. Iodine (atomic symbol: I, atomic number: 53) is a Block P, Group 17, Period 5 element with an atomic radius of 126.90447. The number of electrons in each of Iodine's shells is 2, 8, 18, 18, 7 and its electron configuration is [Kr] 4d10 5s2 5p5. The iodine atom has a radius of 140 pm and a Van der Waals radius of 198 pm. In its elemental form, iodine has a lustrous metallic gray appearance as a solid and a violet appearance as a gas or liquid solution. Elemental IodineIodine forms compounds with many elements, but is less active than the other halogens. It dissolves readily in chloroform, carbon tetrachloride, or carbon disulfide. Iodine compounds are important in organic chemistry and very useful in the field of medicine. Iodine was discovered and first isolated by Bernard Courtois in 1811. The name Iodine is derived from the Greek word "iodes" meaning violet.

Copper

See more Copper products. Copper Bohr Model Copper (atomic symbol: Cu, atomic number: 29) is a Block D, Group 11, Period 4 element with an atomic weight of 63.546. The number of electrons in each of copper's shells is 2, 8, 18, 1 and its electron configuration is [Ar]3d10 4s1. The copper atom has a radius of 128 pm and a Van der Waals radius of 186 pm. Copper was first discovered by Early Man prior to 9000 BC. In its elemental form, copper has a reddish-orange metallic and lustrous appearance. Of all pure metals, only silver Elemental Copperhas a higher electrical conductivity. The origin of the word copper comes from the Latin word 'cuprium' which translates as "metal of Cyprus," as the Mediterranean island of Cyprus was known as an ancient source of mined copper..

Bromine

See more Bromine products. Bromine (atomic symbol: Br, atomic number: 35) is a Block P, Group 17, Period 4 element. Its electron configuration is [Ar]4s23d104p5. The bromine atom has a radius of 102 pm and its Van der Waals radius is 183 pm. In its elemental form, bromine Bromine Bohr Model has a red-brown appearance. Bromine does not occur by itself in nature; it is found as colorless soluble crystalline mineral halide salts. Bromine was discovered and first isolated by Antoine Jérôme Balard and Leopold Gmelin in 1825-1826.

Phosphorus

Phosphorus Bohr ModelSee more Phosphorus products. Phosphorus (atomic symbol: P, atomic number: 15) is a Block P, Group 15, Period 3 element. The number of electrons in each of Phosphorus's shells is 2, 8, 5 and its electronic configuration is [Ne] 3s2 3p3. The phosphorus atom has a radius of 110.5.pm and its Van der Waals radius is 180.pm. Phosphorus is a highly-reactive non-metallic element (sometimes considered a metalloid) with two primary allotropes, white phosphorus and red phosphorus its black flaky appearance is similar to graphitic carbon. Compound forms of phosphorus include phosphates and phosphides. Phosphorous was first recognized as an element by Hennig Brand in 1669 its name (phosphorus mirabilis, or "bearer of light") was inspired from the brilliant glow emitted by its distillation.

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