Related Experiment Video
Updated: May 2, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
Two C₂-symmetric chelating P₂-bisphosphazene superbases connected via a binaphthyl backbone--synthesis, structural
Julius F Kögel1, Nis-Julian Kneusels, Jörg Sundermeyer
1Philipps-Universität Marburg, Fachbereich Chemie, Hans-Meerwein-Straße, 35032 Marburg, Germany. jsu@staff.uni-marburg.de.
Abstract:
Two P2-phosphazenyl groups were linked via a C2-symmetric binaphthyl backbone resulting in two novel chiral superbases with dimethylamino and pyrrolidino substituents. We investigated their basic properties and coordination chemistry towards a cationic alkyl aluminum fragment. The outstanding basicity of the chiral tetrasphosphazenes presented herein leads to interesting perspectives for application in asymmetric Brønsted base catalysis.
More Related Videos
Related Concept Videos
π Molecular Orbitals of the Allyl Cation and Anion
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Complexation Equilibria: The Chelate Effect
Acidity of 1-Alkynes
The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
Alkyl Halides
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

