[6+2] Cycloaddition of N -phenyltriazolinedione with cycloheptatriene derivatives mediated and stereodirected by a chiral 3-oxy substituent

Sügimura, Takashi; Im, Chun Young; Okuyama, Tadashi

doi:10.1016/j.tetlet.2003.12.044

Cited by 6 publications

(2 citation statements)

References 14 publications

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“…Therefore, throughout the temperature range 25–100°C in reaction 1 + 5 the formation only adduct 15 should be expected. Other reaction channels have been proposed . The [2π +2π +2π]‐cycloaddition of 1 at C 2 , C 5 atoms of nonconjugated norbornadiene is well known.…”

Section: Resultsmentioning

confidence: 99%

“…The [2π +2π +2π]‐cycloaddition of 1 at C 2 , C 5 atoms of nonconjugated norbornadiene is well known. Assuming a similar cycloaddition of dienophile 1 at C 2 ,C 5 atoms of the nonconjugated, the sterically accessible coplanar system of triene 5 , going through the transition state 19 , the formation of adduct 15 can be suggested (Scheme ). However, the rate constant of reaction 1 with triene 5 (entry 3, Table ) is almost two thousand times larger than that of 1 in the reaction with norbornadiene (entry 18, Table ).…”

Section: Resultsmentioning

confidence: 99%

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Cyclic and Acyclic N═N Bonds in Reactions with Some Alkenes and Dienes

Kiselev

Kornilov

Коновалов

2017

Int. J. Chem. Kinet.

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The kinetics of the Diels–Alder (DA) reactions of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione 1, trans‐diethyl azodicarboxylate 2, and tetracyanoethene 3 with 1,3‐cyclohexadiene 4, cycloheptatriene 5, 1,3‐cycloheptadiene 6, cyclooctatetraene 7, and 1,3‐cyclooctadiene 8 in a range of temperatures and pressures has been studied. Values of the enthalpy, entropy, and volume of activation, as well as the enthalpy and volume of reaction have been obtained. Observed reaction rates of 5+1 and 7+1 have been compared with the known rate of norcaradiene 17 formation in the equilibrium 5⇌17, and that of bicyclo[4,2,0]‐octa‐2,4,7‐triene 20 in the equilibrium 7⇌20. The kinetic data show that the rate of formation of 17 from 5 is much greater than the loss rate of dienophile 1 in reaction of 5+1. In contrast, the formation rate of tautomer 20 is less than the loss rate of dienophile 1 in reaction of 7+1. This reflects that the consecutive reaction of 5 → 17 (+1) → 15 is possible whereas the consecutive reaction of 7 → 20 (+1) → 22 does not occur as the only way.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Cyclic and Acyclic N═N Bonds in Reactions with Some Alkenes and Dienes

Kiselev

Kornilov

Коновалов

2017

Int. J. Chem. Kinet.

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[m+n(+…)] Cycloaddition

2010

Comprehensive Organic Name Reactions and Reagents

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The cycloaddition reaction is an important reaction in organic synthesis, in which two or more molecules combine and form new ring structures, along with the formation of multiple bonds and multiple stereogenic centers in a single step. Besides this, cycloadditions are also considered the right choice when high regioselectivities, chemoselectivities and stereoselectivities are concerned. The present study represents various types of cycloadditions reactions and their mechanism currently used in organic syntheses.

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Bicyclic Systems with Two Bridgehead (Ring Junction) Nitrogen Atoms

Rádl

2008

Comprehensive Heterocyclic Chemistry III

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[6+2] Cycloaddition of N -phenyltriazolinedione with cycloheptatriene derivatives mediated and stereodirected by a chiral 3-oxy substituent

Cited by 6 publications

References 14 publications

Cyclic and Acyclic N═N Bonds in Reactions with Some Alkenes and Dienes

Cyclic and Acyclic N═N Bonds in Reactions with Some Alkenes and Dienes

[m+n(+…)] Cycloaddition

Bicyclic Systems with Two Bridgehead (Ring Junction) Nitrogen Atoms

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