Publication

Verlaufen 1,3-Eliminierungen konzertiert oder nicht ?

Manfred Schlosser
1974
Journal Articles

Abstract

PrCHBrCH2CHPrR (R = Br, F, or I) were converted into 1,2-dipropylcyclopropane by various metallic or organometallic reducing agents. Normally, cyclization occurred in a stereoconvergent manner, i.e. diastereomeric dihalides usually led to the same mixt. of cis-trans isomeric reaction products, indicating a nonconcerted cleavage of the 2 halogen atoms. The isomer ratios depended very strongly on the nature of the reducing agents and on possible salt additives, probably typical for reactions of short-lived intermediates and compatible with the assumed one-electron transfer mechanism. The "endo tendency" was obsd. again: the cis-disubstituted cyclopropane though thermodynamically less stable than the trans isomer was formed predominantly in most cases. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/1ed7afb0-0834-44df-b3fb-512ec80ade38

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Manfred Schlosser
1974
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/1ed7afb0-0834-44df-b3fb-512ec80ade38

About this result

Related concepts (31)

Reducing agent

In chemistry, a reducing agent (also known as a reductant, reducer, or electron donor) is a chemical species that "donates" an electron to an (called the , , , or ). Examples of substances that are common reducing agents include the alkali metals, formic acid, oxalic acid, and sulfite compounds. In their pre-reaction states, reducers have extra electrons (that is, they are by themselves reduced) and oxidizers lack electrons (that is, they are by themselves oxidized). This is commonly expressed in terms of their oxidation states.

Halogen

The halogens (ˈhælədʒən,ˈheɪ-,-loʊ-,_-ˌdʒɛn) are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts), though some authors would exclude tennessine as its chemistry is unknown and is theoretically expected to be more like that of gallium. In the modern IUPAC nomenclature, this group is known as group (XVII) or group (VII). The word "halogen" means "salt former" or "salt maker".

Cis–trans isomerism

Cis–trans isomerism, also known as geometric isomerism or configurational isomerism, is a term used in chemistry that concerns the spatial arrangement of atoms within molecules. The prefixes "cis" and "trans" are from Latin: "this side of" and "the other side of", respectively. In the context of chemistry, cis indicates that the functional groups (substituents) are on the same side of some plane, while trans conveys that they are on opposing (transverse) sides.

Related publications (3)

Verlaufen 1,3-Eliminierungen konzertiert oder nicht ?

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Quantification and analysis of intramolecular interactions

tBuP(NH2)2 - a reactive synthon for the synthesis of molecular imidophosphinates of group 13 metals

Selective syntheses with organometallics. Part X. A convenient and diastereoselective route to homoallyl alcohols: addition of (Z)- or (E)-alkenyldimethoxyboranes to aldehydes