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Organic reaction in which a pi bond and sigma bond are interconverted
In organic chemistry, an electrocyclic reaction is a type of pericyclic, rearrangement reaction where the net result is one pi bond being converted into
Electrocyclic_reaction
Set of rules pertaining to pericyclic reactions
certain electrocyclic reactions might help, as such reactions exhibited striking stereospecificity, but could not predict which stereoisomer a reaction might
Woodward–Hoffmann_rules
Classification of electrocyclic reactions by how end groups are rotated
In organic chemistry, an electrocyclic reaction can either be classified as conrotatory or disrotatory based on the rotation at each end of the molecule
Conrotatory_and_disrotatory
Chemical theory
that twist is not possible and the reaction is not allowed. An electrocyclic reaction is a pericyclic reaction involving the net loss of a pi bond and
Frontier molecular orbital theory
Frontier_molecular_orbital_theory
Sub-discipline of chemistry
reactions are electrocyclic reactions, radical reactions, photoisomerization, and Norrish reactions. Alkenes undergo many important reactions that proceed
Photochemistry
Chemical reaction used in organic chemistry
the reaction mechanism involves a cationic 4π-electrocyclic ring closure which forms the cyclopentenone product (See Mechanism below). As the reaction has
Nazarov_cyclization
Reaction with a cyclic transition state
a pericyclic reaction is the type of organic reaction wherein the transition state of the molecule has a cyclic geometry, the reaction progresses in
Pericyclic_reaction
Chemical process
process in cascade transformations, pericyclic reactions include cycloadditions, electrocyclic reactions and sigmatropic rearrangements. Although some
Cascade_reaction
Hydrocarbon compound containing a non-aromatic ring with a C=C bond
result of this reaction. Reactions of conjugated double-bond systems can be synthesized into cycloalkenes through electrocyclic reactions. Addition of heat
Cycloalkene
Chemical reaction
aromatic ring. The ring expansion occurs in the second step, with an electrocyclic reaction opening the cyclopropane ring to form the 7-membered ring. and material
Buchner_ring_expansion
Preference of an electrocyclic reaction towards inward or outward rotation of substituents
in electrocyclic reactions, defined as "the preference for inward or outward rotation of substituents in conrotatory or disrotatory electrocyclic reactions
Torquoselectivity
Chemical reaction
ring-opening via an electrocyclic reaction (at least formally) to give the allene. Several different mechanisms for the electrocyclic rearrangement have
Doering–LaFlamme allene synthesis
Doering–LaFlamme_allene_synthesis
Process that leads to chemical changes
637–647. Woodward, R.B.; Hoffmann, R. (1965). "Stereochemistry of Electrocyclic Reactions". Journal of the American Chemical Society. 87 (2): 395–397. Bibcode:1965JAChS
Chemical_reaction
Class of photochromic organic compounds
isomer, the E isomer can also undergo a photochemically-induced electrocyclic reaction, forming a new ring and becoming a distinctly colored product called
Fulgide
Ehrlich–Sachs reaction Einhorn variant Einhorn–Brunner reaction Elbs persulfate oxidation Elbs reaction Electrochemical fluorination Electrocyclic reaction Electrophilic
List_of_organic_reactions
Intramolecular organic reaction in which a sigma bond is changed
the ring reforms electrocyclically: This same mechanistic process is seen below, without the final electrocyclic ring-closing reaction, in the interconversion
Sigmatropic_reaction
Chemical compound
using a biomimetic strategy involving series of stereocontrolled electrocyclic reactions. Specifically, they observed that the natural products endiandric
Endiandric_acid_C
Method of predicting if a chemical reaction can occur
Woodward, R. B.; Hoffmann, Roald (1965). "Stereochemistry of electrocyclic reactions". J. Am. Chem. Soc. 87: 395–397. doi:10.1021/ja01080a054. Longuet-Higgins
Möbius–Hückel_concept
Essential nutrient
photolyzed by ultraviolet light in a 6-electron conrotatory ring-opening electrocyclic reaction; the product is previtamin D3. Second, previtamin D3 spontaneously
Vitamin_D
Chemical compound
hexaphenylbenzene. The adjacent pairs of benzene rings undergo oxidative electrocyclic reactions and aromatization by oxidation by iron(III) chloride in nitromethane
Hexabenzocoronene
Overview of and topical guide to organic chemistry
Wacker-Tsuji oxidation Cheletropic reaction Dyotropic reaction Electrocyclic reaction Group transfer reaction Sigmatropic reaction Cationic polymerization Anionic
Outline_of_organic_chemistry
Chemical reaction
a 1,2-alkyl shift, to give the ketene product, or can undergo a 4π electrocyclic ring closure, to form an antiaromatic oxirene. This oxirene can reopen
Wolff_rearrangement
Vitamin D3, a chemical compound
the epidermal layer of skin, 7-dehydrocholesterol undergoes an electrocyclic reaction as a result of UVB light at wavelengths between 290 and 310 nm,
Cholecalciferol
Chemical reaction
compound instead first undergoes a tautomerization followed by an electrocyclic reaction to give the same intermediate, which then similarly undergoes a
Elbs_reaction
British chemist and cognitive scientist (1923–2004)
H. C.; Abrahamson, E. W. (1965). "The Electronic Mechanism of Electrocyclic Reactions". Journal of the American Chemical Society. 87 (9): 2045. Bibcode:1965JAChS
Christopher_Longuet-Higgins
Chemical reaction
(and the rate-determining step) in the reaction mechanism is the annulation of the molecule via an electrocyclic ring closing. For this step, the Schiff
Conrad–Limpach_synthesis
Chemical rearrangement
Rosana; de Lera, Ángel R. (2004-09-06). "Theoretical Study of the Electrocyclic Ring Closure of Hydroxypentadienyl Cations". Chemistry – A European
Piancatelli_rearrangement
Chemical compound
this happens under high-dose or prolonged UVB exposure. A disrotatory electrocyclic ring-closure of the cZc conformer results in lumisterol 3 (L3). A cis-trans
Previtamin_D3
Chemical compound
Peter M. (2011). "The Ultrafast Pathway of Photon-Induced Electrocyclic Ring-Opening Reactions: The Case of 1,3-Cyclohexadiene". Annual Review of Physical
1,3,5-Hexatriene
Pericyclic chemical reaction
dipole component. Diastereopure azomethine ylides are generated by electrocyclic ring opening of aziridines, and then rapidly trapped with strong dipolarophiles
1,3-Dipolar_cycloaddition
Chemical compound
1021/ja00536a069. Kikuchi O. (1981). "A classification of the photochemical electrocyclic reactions of heteroatom conjugated systems". Tetrahedron Lett. 22 (9): 859–862
Oxetene
American chemist (born 1928)
"A Claim on the Development of the Frontier Orbital Explanation Electrocyclic Reactions". Angewandte Chemie International Edition. 43 (48): 6586–6590.
Elias_James_Corey
Class of chemical compounds
molecular orbital control of stereochemistry in organometallic electrocyclic reactions". Journal of the Chemical Society, Chemical Communications (1):
Trimethylenemethane_complexes
Chemical compound
cyclobutene. It then underwent a 4-electron electrocyclic ring opening to a 1,3-thiazepine and then a 6-electron electrocyclic ring closing to a 7-thia-2-azanorcaradiene
Thiazole
Chemical compound
norcaradiene ethyl ester, which then undergoes a thermally-allowed electrocyclic ring expansion to give 1,3,5-cycloheptatriene 7-carboxylic acid ethyl
Cycloheptatriene
Classification of pericyclic and electrocyclic chemical reactions
carbon atom of a [1, n]-sigmatropic rearrangement, and conrotation for electrocyclic ring closure, while suprafacial corresponds to retention and disrotation
Antarafacial_and_suprafacial
Form of chemical synthesis
nucleophilic ring closure or a conrotatory electrocyclic ring closure. The second step is different from typical electrocyclic ring closures as predicted by the
Staudinger_synthesis
Chemical compound
stilbene photocyclization, an intramolecular reaction. (Z)-Stilbene can undergo electrocyclic reactions. In strong (protic) acid, cis-stilbene oligomerizes
(Z)-Stilbene
Chemical compound
disrotatory electrocyclic ring-closure. In vivo this happens under high-dose or prolonged UVB exposure. Vitamin D2 can be formed from L2 by an electrocyclic ring
Lumisterol
Functional group made of a carbon-carbon-nitrogen heterocycle
on both carbons form azomethine ylides in an electrocyclic thermal or photochemical ring-opening reaction. These ylides can be trapped with a suitable
Aziridines
Theory of molecular orbitals by Erich Hückel
Organic Chemists, Wiley, New York (1961). "Stereochemistry of Electrocyclic Reactions", R. B. Woodward, Roald Hoffmann, J. Am. Chem. Soc., 1965; 87(2);
Hückel_method
Index of chemical compounds with the same molecular formula
2024-12-08 Kikuchi O. (1981). "A classification of the photochemical electrocyclic reactions of heteroatom conjugated systems". Tetrahedron Lett. 22 (9): 859–862
C3H4O
I. (4 December 2015). "Woodward–Hoffmann's Stereochemistry of Electrocyclic Reactions: From Day 1 to the JACS Receipt Date (May 5, 1964 to November 30
Jeffrey_I._Seeman
Indian photochemist (1928–2019)
the organic reactions and functional group transformations, heterohexa-1, 3, 5-triene systems with regard to its electrocyclic reactions and the synthetic
M._V._George
Class of chemical compounds
Fe(CO)3[η4-1,3-butadiene]. At high temperatures, benzocyclobutenes undergo electrocyclic ring-opening to form o-xylylenes. This and other syntheses of o-xylylenes
Xylylene
Organic chemical transformation
formation of a bis-π-allyl complex precede electrocyclic ring closure and catalyst release. (3) Reactions of divinylcyclopropanes containing substituted
Divinylcyclopropane-cycloheptadiene rearrangement
Divinylcyclopropane-cycloheptadiene_rearrangement
Chemical compound
cyclooctatetraene (1) undergoes thermal, electrocyclic isomerization (to 2), followed by a Diels–Alder reaction with maleic anhydride (3). [2 + 2] photochemical
Basketene
photochemically driven electrocyclic ring-closure of hexa-2,4-diene, which proceeds in a disrotatory fashion. Organic reactions that obey these rules are
Organic_photochemistry
Chemical compound
side reaction in the production of allyl radicals from propene and oxalyl chloride. As a reaction intermediate, it is produced from electrocyclic ring-opening
1,3-Butadienal
Chemical reaction used to create phenols
four subsequent pericyclic reactions (Scheme 3). Heating a cyclobutenone above 80 °C initiates a four-electron electrocyclic cleavage generating a vinyl
Danheiser_benzannulation
Chemical compound
C−C bonds. Electrocyclic ring opening of cyclobutenones yields vinylketenes, which serve as reactive intermediates in cycloaddition reactions. Unsubstituted
Cyclobutenone
Chemical reaction which adds a –CH2– group to a molecule
the case of arenes, the cyclopropanation product undergoes further electrocyclic ring opening to give cycloheptatriene products (Buchner ring expansion)
Methylenation
Photochromic organic chemical compound
in the other one the ring is opened. The photochromism arises from electrocyclic cleavage of the C-spiro-O bond. Photochromism is the phenomenon that
Spiropyran
Chemical compound
Structure 16 is a transition state proposed to explain the concerted electrocyclic reaction and the carbonyl formation. Herath, K.; Jayasuriya, H.; Bills, G
Integrasone
Chemical compound with four carbon rings sharing a single carbon atom
study describes an unusual 8π disrotatory – 6π conrotatory electrocyclic cascade reaction aiming to minimise the number of steps required to synthesise
Fenestrane
Reactive class of chemicals
that catalyse ketene polymerisation. Vinylketenes may be prepared by electrocyclic ring opening of cyclobutenones. In the Danheiser benzannulation, vinylketene
Vinylketenes
Chemical compound
undergo electrocyclic ring-opening to form o-xylylenes. These structures were not isolated—they immediately react via [4+4] cycloaddition reactions to form
Superphane
Reversible chemical transformation by absorption of electromagnetic radiation
Some rely on irradiation for the reverse reaction, others use thermal activation for the reverse reaction. Some quinones, and phenoxynaphthacene quinone
Photochromism
Indian chemist
O. (16 December 2011). "One-Flask Tethered Ring Closing Metathesis–Electrocyclic Ring Opening for the Highly Stereoselective Synthesis of Conjugated
Dhevalapally_B._Ramachary
Group of chemical compounds
adducts. The proposed biosynthetic pathway is thought to involve: (a) an electrocyclic ring closure of 3, followed by (b) an enzymatic oxidation to furnish
Torreyanic_acid
Molecule with ability to reversibly switch states
(November 2017), "Principles of Photochemical Reactions", Essentials of Pericyclic and Photochemical Reactions, Lecture Notes in Chemistry, vol. 93, Cham:
Molecular_switch
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