Publication

Preferred syn-elimination from trans-1,2-dichloro- and trans-1,2-dibromocyclodecane

Manfred Schlosser
1971
Journal Articles

Abstract

syn-Coplanar cleavage of hydrogen halide, esp. the syn -> trans process, was favored in the dehydrohalogenation of trans-1,2-dichlorocyclodecane and trans-1,2-dibromocyclodecane, and the anti elimination, which was most favored with acyclic compds., was retarded. The transition state for syn elimination was thought to be stabilized by redn. in transannular repulsive forces. The dehydrohalogenation rate depended only slightly on the solvent. [on SciFinder (R)]

Official source

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Manfred Schlosser
1971
Journal Articles

Abstract

Official source

Related concepts (22)

Syn and anti addition

In organic chemistry, syn- and anti-addition are different ways in which substituent molecules can be added to an alkene () or alkyne (). 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.

Hydrogen halide

In chemistry, hydrogen halides (hydrohalic acids when in the aqueous phase) are diatomic, inorganic compounds that function as Arrhenius acids. The formula is HX where X is one of the halogens: fluorine, chlorine, bromine, iodine, or astatine. All known hydrogen halides are gases at Standard Temperature and Pressure. The hydrogen halides are diatomic molecules with no tendency to ionize in the gas phase (although liquified hydrogen fluoride is a polar solvent somewhat similar to water).

Dehydrohalogenation

In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Traditionally, alkyl halides are substrates for dehydrohalogenations. The alkyl halide must be able to form an alkene, thus halides having no C–H bond on an adjacent carbon are not suitable substrates. Aryl halides are also unsuitable. Upon treatment with strong base, chlorobenzene dehydrohalogenates to give phenol via a benzyne intermediate.