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Phosphorus tribromide, like PCl 3 and PF 3, has both properties of a Lewis base and a Lewis acid. For example, with a Lewis acid such as boron tribromide it forms stable 1 :1 adducts such as Br 3 B · PBr 3. At the same time PBr 3 can react as an electrophile or Lewis acid in many of its reactions, for example with amines.
The reaction mechanism of the Mitsunobu reaction is fairly complex. The identity of intermediates and the roles they play has been the subject of debate. Initially, the triphenyl phosphine (2) makes a nucleophilic attack upon diethyl azodicarboxylate (1) producing a betaine intermediate 3, which deprotonates the carboxylic acid (4) to form the ion pair 5.
As a general approach, one can simply draw the transition state of the reaction. For a sigmatropic reaction, the transition state will consist of two fragments, joined by the forming and breaking σ-bonds. The sigmatropic reaction is named as a [i,j]-sigmatropic rearrangement (i ≤ j) if these two fragments consist of i and j atoms. This is ...
The observed rotation of the sample is the weighted sum of the optical rotation of each anomer weighted by the amount of that anomer present. Therefore, one can use a polarimeter to measure the rotation of a sample and then calculate the ratio of the two anomers present from the enantiomeric excess, as long as one knows the rotation of each pure anomer.
In stereochemistry, torquoselectivity is a special kind of stereoselectivity observed in electrocyclic reactions, defined as "the preference for inward or outward rotation of substituents in conrotatory or disrotatory electrocyclic reactions."
Chiral inversion is the process of conversion of one enantiomer of a chiral molecule to its mirror-image version with no other change in the molecule. [1] [2] [3] [4]Chiral inversion happens depending on various factors (viz. biological-, solvent-, light-, temperature- induced, etc.) and the energy barrier energy barrier associated with the stereogenic element present in the chiral molecule. 2 ...
An example of the Hell–Volhard–Zelinsky reaction can be seen in the preparation of alanine from propionic acid.In the first step, a combination of bromine and phosphorus tribromide is used in the Hell–Volhard–Zelinsky reaction to prepare 2-bromopropionic acid, [3] which in the second step is converted to a racemic mixture of the amino acid product by ammonolysis.
Thermolysis converts 1 to (E,E) geometric isomer 2, but 3 to (E,Z) isomer 4.. The Woodward–Hoffmann rules (or the pericyclic selection rules) [1] are a set of rules devised by Robert Burns Woodward and Roald Hoffmann to rationalize or predict certain aspects of the stereochemistry and activation energy of pericyclic reactions, an important class of reactions in organic chemistry.