The Rate of Reaction of Maleic Anhydride with 1,3-Dienes as Related to Diene Conformation

Craig, D. P.; Shipman, J. J.; Fowler, Ray B.

doi:10.1021/ja01474a023

Cited by 124 publications

(44 citation statements)

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“…These dienes include the following: ( E )‐1‐X‐butadienes (BDs) and 2‐X‐BDs, 1‐X‐cyclopentadienes (CPs) and 2‐X‐CP, α ‐X‐furans and β ‐X‐furans, α ‐X‐pyroles and β ‐X‐pyroles (their concerted exo and endo TSs are illustrated in chart ). It is known that numerous D–A reactions of different dienes with MA have been investigated experimentally and theoretically from different aspects,, but investigations of the substituent electronic effects on the endo–exo selectivity have been few documented in our knowledge.…”

Section: Introductionmentioning

confidence: 99%

Substituent effects in the Diels–Alder reactions of butadienes, cyclopentadienes, furans and pyroles with maleic anhydride

Qiu

2015

J of Physical Organic Chem

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In this study, activation energies in the Diels–Alder reactions of a series of substituted butadienes, cyclopentadienes, furans and pyroles with maleic anhydride were calculated by the M06‐2X/6‐31G(d) method. The substituent effects on the reactivity and the endo–exo selectivity have been examined. The strength of reactivity effect has an order of pyroles > furans > cyclopentadienes > butadienes, which is highly correlated with the lowest unoccupied molecular orbital energy, the electronic chemical potential and the electrophilicity of parent diene but relatively less correlated with the highest occupied molecular orbital energy and chemical hardness. The trend that an increase of necleophilicity caused by an electron‐donating group on the diene favors the endo TS is effective with C2 substitution. With C1 substitution, the trend is ambiguous or even opposite. Copyright © 2015 John Wiley & Sons, Ltd.

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Section: Introductionmentioning

confidence: 99%

Substituent effects in the Diels–Alder reactions of butadienes, cyclopentadienes, furans and pyroles with maleic anhydride

Qiu

2015

J of Physical Organic Chem

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“…With the latter, cyclopentadiene is reported to be 1.35 x lo3 times more reactive than buta-1.3-diene (8). The two dienes 3 , I…”

Section: The Cationmentioning

confidence: 97%

The cyclopentadienide anion and tropylium cation analogs of triptycene

Butler¹,

Gupta²

1978

Can. J. Chem.

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“…isoprene [Craig et al, 1961;Hsu et al, 1969]. The conformation of the monomer need not translate into polymer stereochemistry since isomerization is possible after the s-trans or s-cis conformer adds to a propagating center.…”

Section: Ila Ilbmentioning

confidence: 99%

Stereochemistry of Polymerization

Odian

2004

Principles of Polymerization

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Constitutional (formerly: structural) isomerism is encountered when polymers have the same overall chemical composition (i.e., same molecular formula) but differ in connectivitythe order in which the atoms are connected to each other. Polyacetaldehyde, poly(ethylene oxide), and poly(vinyl alcohol) are constitutional isomers. The first two polymers are CH CH 3 O C H 2 CH OH CH 2 CH 2 O n n Polyacetaldehyde Poly(ethylene oxide) Poly(vinyl alcohol) n obtained from isomeric monomers, acetaldehyde and ethylene oxide. The third is obtained by hydrolysis of poly(vinyl acetate) since vinyl alcohol does not exist (it is the enol form of acetaldehyde). Poly(methyl methacrylate) and poly(ethyl acrylate) are isomeric polymers CH 2 C CH 3 CO 2 CH 3 CH 2 CH CO 2 C 2 H 5 n n Poly (methyl methacrylate) Poly (ethyl acrylate) formed from isomeric monomers. Poly(E-caprolactam) and poly(hexamethylene adipamide) are isomeric even though the monomers are not isomeric. Similarly, the 1 : 1 copolymer of Principles of Polymerization, Fourth Edition.

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The Rate of Reaction of Maleic Anhydride with 1,3-Dienes as Related to Diene Conformation

Cited by 124 publications

References 2 publications

Substituent effects in the Diels–Alder reactions of butadienes, cyclopentadienes, furans and pyroles with maleic anhydride

Substituent effects in the Diels–Alder reactions of butadienes, cyclopentadienes, furans and pyroles with maleic anhydride

The cyclopentadienide anion and tropylium cation analogs of triptycene

Stereochemistry of Polymerization

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