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The concepts of syn and anti addition are used to characterize the different reactions of organic chemistry by reflecting the stereochemistry of the products in a reaction. The type of addition that occurs depends on multiple different factors of a reaction, and is defined by the final orientation of the substituents on the parent molecule .
Reactions of conjugated double-bond systems can be synthesized into cycloalkenes through electrocyclic reactions. [13] Addition of heat or photolysis causes a reversible reaction that causes one pi bond to become a sigma bond, which closes the ring and creates a cycloalkene. [11] Formation of a cycloalkane via an electrocyclic reaction
Cycloisomerization is a very broad topic in organic synthesis and many reactions that would be categorized as such exist. Two basic classes of these reactions are intramolecular Michael addition and Intramolecular Diels–Alder reactions. Under the umbrella of cycloisomerization, enyne and related olefin cycloisomerizations are the most widely ...
Cyclopropanation is also stereospecific as the addition of carbene and carbenoids to alkenes is a form of a cheletropic reaction, with the addition taking place in a syn manner. For example, dibromocarbene and cis-2-butene yield cis-2,3-dimethyl-1,1-dibromocyclopropane, whereas the trans isomer exclusively yields the trans cyclopropane. [16]
For example, an analog for the Diels-Alder reaction is the quadricyclane-DMAD reaction: In the (i+j+...) cycloaddition notation i and j refer to the number of atoms involved in the cycloaddition. In this notation, a Diels-Alder reaction is a (4+2)cycloaddition and a 1,3-dipolar addition such as the first step in ozonolysis is a (3+2)cycloaddition.
In addition to terminal alkenes, tri- and tetrasubstituted alkenes have been used in RCM reactions to afford substituted cyclic olefin products. [32] Ring-closing metathesis has also been used to cyclize rings containing an alkyne to produce a new terminal alkene , or even undergo a second cyclization to form bicycles.
In summary, experimental evidence seems to support that syn-addition occurs under low-chloride reaction concentrations (< 1 mol/L, industrial process conditions), while anti-addition occurs under high-chloride (> 3mol/L) reaction concentrations, probably due to chloride ions saturating the catalyst and inhibiting the inner-sphere mechanism ...
The reaction follows Markovnikov's rule (the hydroxy group will always be added to the more substituted carbon). The oxymercuration part of the reaction involves anti addition of OH group but the demercuration part of the reaction involves free radical mechanism and is not stereospecific, i.e. H and OH may be syn or anti to each other. [2] [3] [4]