In organic chemistry, an electrocyclic reaction is a type of pericyclic rearrangement where the net result is one pi bond being converted into one sigma bond or vice versa.[1] These reactions are usually categorized by the following criteria:
Reactions can be either photochemical or thermal.
Reactions can be either ring-opening or ring-closing (electrocyclization).
Depending on the type of reaction (photochemical or thermal) and the number of pi electrons, the reaction can happen through either a conrotatory or disrotatory mechanism.
The type of rotation determines whether the cis or trans isomer of the product will be formed.
^IUPAC Gold Book
and 27 Related for: Electrocyclic reaction information
In organic chemistry, an electrocyclicreaction is a type of pericyclic rearrangement where the net result is one pi bond being converted into one sigma...
that twist is not possible and the reaction is not allowed. An electrocyclicreaction is a pericyclic reaction involving the net loss of a pi bond and...
An electrocyclicreaction can either be classified as conrotatory or disrotatory based on the rotation at each end of the molecule. In conrotatory mode...
a pericyclic reaction is the type of organic reaction wherein the transition state of the molecule has a cyclic geometry, the reaction progresses in...
the ring reforms electrocyclically: This same mechanistic process is seen below, without the final electrocyclic ring-closing reaction, in the interconversion...
organic reactions are electrocyclicreactions, radical reactions, photoisomerization, and Norrish reactions. Alkenes undergo many important reactions that...
process in cascade transformations, pericyclic reactions include cycloadditions, electrocyclicreactions and sigmatropic rearrangements. Although some...
the reaction mechanism involves a cationic 4π-electrocyclic ring closure which forms the cyclopentenone product (See Mechanism below). As the reaction has...
result of this reaction. Reactions of conjugated double-bond systems can be synthesized into cycloalkenes through electrocyclicreactions. Addition of heat...
637–647 Woodward, R.B.; Hoffmann, R. (1965). "Stereochemistry of ElectrocyclicReactions". Journal of the American Chemical Society. 87 (2): 395–397. doi:10...
second step, with an electrocyclicreaction opening the cyclopropane ring to form the 7-membered ring. The Buchner ring expansion reaction was first used in...
their high thermodynamic stability. They operate by means of a 6-pi electrocyclicreaction, the thermal analog of which is impossible due to steric hindrance...
the epidermal layer of skin, 7-dehydrocholesterol undergoes an electrocyclicreaction as a result of UVB light at wavelengths between 290 and 315 nm,...
photolyzed by ultraviolet light in a 6-electron conrotatory ring-opening electrocyclicreaction; the product is previtamin D3. Second, previtamin D3 spontaneously...
compound instead first undergoes a tautomerization followed by an electrocyclicreaction to give the same intermediate, which then similarly undergoes a...
1021/ja00536a069. Kikuchi O. (1981). "A classification of the photochemical electrocyclicreactions of heteroatom conjugated systems". Tetrahedron Lett. 22 (9): 859–862...
Torquoselectivity is a special kind of stereoselectivity observed in electrocyclicreactions in organic chemistry, defined as "the preference for inward or...
2-furyl carbinols. It was proposed by Piancatelli that the reaction is a thermal electrocyclicreaction of a conrotatory 4π electron system while studying specifics...
hexaphenylbenzene. The adjacent pairs of benzene rings undergo oxidative electrocyclicreactions and aromatization by oxidation by iron(III) chloride in nitromethane...
photochemically driven electrocyclic ring-closure of hexa-2,4-diene, which proceeds in a disrotatory fashion. Organic reactions that obey these rules are...
molecular orbital control of stereochemistry in organometallic electrocyclicreactions". Journal of the Chemical Society, Chemical Communications (1):...
isomer, the E isomer can also undergo a photochemically-induced electrocyclicreaction, forming a new ring and becoming a distinctly colored product called...
3-thiazepine in a 4-electron electrocyclic ring opening and then to a 7-thia-2-azanorcaradiene in a 6-electron electrocyclic ring, closing before extruding...
first to produce a zwitterionic oxyallyl cation before a disrotatory electrocyclic ring closure takes place to afford the cyclopropanone intermediate....
"A Claim on the Development of the Frontier Orbital Explanation ElectrocyclicReactions". Angewandte Chemie International Edition. 43 (48): 6586–6590....
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