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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 ]
The most stable trans-isomers of 10 ring or greater cycloalkenes exhibit 4 irregularities from standard geometric norms. The first irregularity is twisted planes of substituents along the C=C. Using C=C as the stable axis, 2 substituents of 1 carbon can be visualized on the same plane, equally applied to the other carbon.
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):
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
Structure of (acac)Rh(C 2 H 4)(C 2 F 4), distances (red) in picometers. [3]The bonding between alkenes and transition metals is described by the Dewar–Chatt–Duncanson model, which involves donation of electrons in the pi-orbital on the alkene to empty orbitals on the metal.
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. cis -Cyclooctene
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 ...