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trans-Cyclooctene is a cyclic hydrocarbon with the formula [–(CH 2) 6 CH=CH–], where the two C–C single bonds adjacent to the double bond are on opposite sides of the latter's plane. It is a colorless liquid with a disagreeable odor. Cyclooctene is notable as the smallest cycloalkene that is readily isolated as its trans-isomer.
Cyclooctene is notable because it is the smallest cycloalkene that can exist stably as either the cis or trans stereoisomer, with cis-cyclooctene being the most common. Theoretical analysis implies a total of 16 conformational and configurational isomers, all chiral, forming 8 enantiomeric pairs. [ 1 ]
BINOL is a typical example of an axially chiral molecule, while trans-cyclooctene is a commonly cited example of a planar chiral molecule. Finally, helicene possesses helical chirality, which is one type of inherent chirality. Chirality is an important concept for stereochemistry and biochemistry
An example of a Hofmann elimination (not involving a contrast between a Zaitsev product and a Hofmann product) is the synthesis of trans-cyclooctene. [4] The trans isomer is selectively trapped as a complex with silver nitrate (in this diagram the trans form looks like a cis form, but see the trans-cyclooctene article for better images):
In organic chemistry, a cycloalkene or cycloolefin is a type of alkene hydrocarbon which contains a closed ring of carbon atoms and either one or more double bonds, but has no aromatic character. Some cycloalkenes, such as cyclobutene and cyclopentene , can be used as monomers to produce polymer chains. [ 1 ]
It is a colorless liquid that is used industrially to produce a polymer. It is also a ligand in organometallic chemistry. Cyclooctene is the smallest cycloalkene that can be isolated as both the cis- and trans-isomer. [2] cis-Cyclooctene is shaped like the 8-carbon equivalent chair conformation of cyclohexane.
Very often, cis–trans stereoisomers contain double bonds or ring structures. In both cases the rotation of bonds is restricted or prevented. [4] When the substituent groups are oriented in the same direction, the diastereomer is referred to as cis, whereas when the substituents are oriented in opposing directions, the diastereomer is referred to as trans.
Small trans-cycloalkenes have so much ring strain they cannot exist for extended periods of time. [9] For instance, the smallest trans-cycloalkane that has been isolated is trans-cyclooctene. Trans-cycloheptene has been detected via spectrophotometry for minute time periods, and trans-cyclohexene is thought to be an intermediate in some ...