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- https://chem.libretexts.org/Courses/can/CHEM_232_-_Organic_Chemistry_II_(Puenzo)/15%3A_Orbitals_and_Organic_Chemistry_-_Pericyclic_Reactions/15.06%3A_Cycloaddition_ReactionsA concerted combination of two π-electron systems to form a ring of atoms having two new σ bonds and two fewer π bonds is called a cycloaddition reaction. The number of participating π-electrons in ea...A concerted combination of two π-electron systems to form a ring of atoms having two new σ bonds and two fewer π bonds is called a cycloaddition reaction. The number of participating π-electrons in each component is given in brackets preceding the name of the reaction. The Diels-Alder reaction is the most useful cycloaddition reaction due to the ubiquity of 6-membered rings and its ability to reliably control stereochemistry in the product.
- https://chem.libretexts.org/Courses/Smith_College/CHM_223_Chemistry_III%3A_Organic_Chemistry_(2024)/09%3A_Orbitals_and_Organic_Chemistry_-_Pericyclic_Reactions/9.05%3A_Cycloaddition_ReactionsA concerted combination of two π-electron systems to form a ring of atoms having two new σ bonds and two fewer π bonds is called a cycloaddition reaction. The number of participating π-electrons in ea...A concerted combination of two π-electron systems to form a ring of atoms having two new σ bonds and two fewer π bonds is called a cycloaddition reaction. The number of participating π-electrons in each component is given in brackets preceding the name of the reaction. The Diels-Alder reaction is the most useful cycloaddition reaction due to the ubiquity of 6-membered rings and its ability to reliably control stereochemistry in the product.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(OpenStax)/14%3A_Conjugated_Compounds_and_Ultraviolet_Spectroscopy/14.05%3A_Characteristics_of_the_Diels-Alder_ReactionThe Diels–Alder cycloaddition reaction occurs most rapidly if the alkene component, called the dienophile (“diene lover”), has an electron-withdrawing substituent group. Thus, ethylene itself reacts s...The Diels–Alder cycloaddition reaction occurs most rapidly if the alkene component, called the dienophile (“diene lover”), has an electron-withdrawing substituent group. Thus, ethylene itself reacts sluggishly, but propenal, ethyl propenoate, maleic anhydride, benzoquinone, propenenitrile, and similar compounds are highly reactive. Note also that alkynes, such as methyl propynoate, can act as Diels–Alder dienophiles.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(Morsch_et_al.)/14%3A_Conjugated_Compounds_and_Ultraviolet_Spectroscopy/14.05%3A_Characteristics_of_the_Diels-Alder_ReactionFor many acyclic dienes the s-trans conformer is more stable than the s-cis conformer (due to steric crowding of the end groups), but the two are generally in rapid equilibrium, permitting the use of ...For many acyclic dienes the s-trans conformer is more stable than the s-cis conformer (due to steric crowding of the end groups), but the two are generally in rapid equilibrium, permitting the use of all but the most hindered dienes as reactants in Diels-Alder reactions. Similarly to the effects of dienophile stereochemistry, the positioning of substituents on the 1 and 4 carbons in the diene determine the stereochemistry in the product.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)/13%3A_Polyfunctional_Compounds_Alkadienes_and_Approaches_to_Organic_Synthesis/13.03%3A_Cycloaddition_ReactionsThere are a variety of reactions whereby rings are formed through addition to double or triple bonds. Diels-Alder reaction, which has proved so valuable in synthesis, is the most famous and can be cal...There are a variety of reactions whereby rings are formed through addition to double or triple bonds. Diels-Alder reaction, which has proved so valuable in synthesis, is the most famous and can be called a [4 + 2] cycloaddition and results in the formation of a six-membered ring.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(Morsch_et_al.)/29%3A_Orbitals_and_Organic_Chemistry_-_Pericyclic_Reactions/29.05%3A_Cycloaddition_ReactionsA concerted combination of two π-electron systems to form a ring of atoms having two new σ bonds and two fewer π bonds is called a cycloaddition reaction. The number of participating π-electrons in ea...A concerted combination of two π-electron systems to form a ring of atoms having two new σ bonds and two fewer π bonds is called a cycloaddition reaction. The number of participating π-electrons in each component is given in brackets preceding the name of the reaction. The Diels-Alder reaction is the most useful cycloaddition reaction due to the ubiquity of 6-membered rings and its ability to reliably control stereochemistry in the product.
- https://chem.libretexts.org/Courses/Smith_College/CHM_223_Chemistry_III%3A_Organic_Chemistry_(2024)/08%3A_Conjugated_Compounds_and_Ultraviolet_Spectroscopy/8.06%3A_Characteristics_of_the_Diels-Alder_ReactionFor many acyclic dienes the s-trans conformer is more stable than the s-cis conformer (due to steric crowding of the end groups), but the two are generally in rapid equilibrium, permitting the use of ...For many acyclic dienes the s-trans conformer is more stable than the s-cis conformer (due to steric crowding of the end groups), but the two are generally in rapid equilibrium, permitting the use of all but the most hindered dienes as reactants in Diels-Alder reactions. Similarly to the effects of dienophile stereochemistry, the positioning of substituents on the 1 and 4 carbons in the diene determine the stereochemistry in the product.
- https://chem.libretexts.org/Workbench/LCDS_Organic_Chemistry_OER_Textbook_-_Todd_Trout/14%3A_Conjugated_Compounds_and_Ultraviolet_Spectroscopy/14.06%3A_Characteristics_of_the_Diels-Alder_ReactionA substituent on one bridge is said to be endo if it is syn (cis) to the larger of the other two bridges and is said to be exo if it is anti (trans) to the larger of the other two. Endo products resul...A substituent on one bridge is said to be endo if it is syn (cis) to the larger of the other two bridges and is said to be exo if it is anti (trans) to the larger of the other two. Endo products result from Diels–Alder reactions because the amount of orbital overlap between diene and dienophile is greater when the reactants lie directly on top of one another, so that the electron-withdrawing substituent on the dienophile is underneath the diene double bonds.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_II_(Morsch_et_al.)/14%3A_Conjugated_Compounds_and_Ultraviolet_Spectroscopy/14.05%3A_Characteristics_of_the_Diels-Alder_ReactionFor many acyclic dienes the s-trans conformer is more stable than the s-cis conformer (due to steric crowding of the end groups), but the two are generally in rapid equilibrium, permitting the use of ...For many acyclic dienes the s-trans conformer is more stable than the s-cis conformer (due to steric crowding of the end groups), but the two are generally in rapid equilibrium, permitting the use of all but the most hindered dienes as reactants in Diels-Alder reactions. Similarly to the effects of dienophile stereochemistry, the positioning of substituents on the 1 and 4 carbons in the diene determine the stereochemistry in the product.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)/22%3A_Arenes_Electrophilic_Aromatic_Substitution/22.09%3A_Addition_Reactions_of_ArenesBenzenoid compounds are not readily converted to cyclohexane derivatives. Nevertheless, several addition reactions are carried out on an industrial scale. Mention was made previously of the hydrogenat...Benzenoid compounds are not readily converted to cyclohexane derivatives. Nevertheless, several addition reactions are carried out on an industrial scale. Mention was made previously of the hydrogenation of benzene to cyclohexane in the presence of a nickel catalyst.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Synthesis_(Shea)/01%3A_Pericyclic_Reactions/1.01%3A_Introduction_to_Pericyclic_ReactionsThis page provides an overview of the three types of pericyclic reactions: cycloadditions, electrocyclic reactions, and sigmatropic rearrangements.
