2000
DOI: 10.1002/(sici)1099-0690(200003)2000:5<743::aid-ejoc743>3.0.co;2-i
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Proximate,syn-Periplanar, Rigid Imine(Nitrone)/Ene-, and Diazene(Diazeneoxy)/Ene Systems: Syntheses, Homoconjugate Reactivity and Photochemistry

Abstract: The chances for intramolecular imine/ene (→ azetidines), diazene/ene (→ 1,2‐diazetidines), diazeneoxy/ene (→ 1,2‐diazetidine oxides) and diazenedioxiene (→ 1,2‐diazetidine dioxides) [2+2]photocycloadditions and for the isolation of the respective photoproducts, have been probed with specifically designed substrates. Upon direct or sensitized excitation, [2+2]cycloaddition was found to be the exclusive or at least dominant chemical process for the CN/CC, NN/CC and ONN(O)/CC systems featuring very small π,… Show more

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Cited by 28 publications
(10 citation statements)
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“…Ene reactions of 7 with various olefins have been reported 23. With certain olefins, compound 7 leads to the formation of 1,2‐azetidines 24ac. Recently, it has been used as a dinitrogen equivalent where it undergoes a [4+2] cycloaddition reaction with aryl ketenimines to yield 1,2,4‐triazolo[1,2‐a]cinnolines 24de…”
Section: Resultsmentioning
confidence: 99%
“…Ene reactions of 7 with various olefins have been reported 23. With certain olefins, compound 7 leads to the formation of 1,2‐azetidines 24ac. Recently, it has been used as a dinitrogen equivalent where it undergoes a [4+2] cycloaddition reaction with aryl ketenimines to yield 1,2,4‐triazolo[1,2‐a]cinnolines 24de…”
Section: Resultsmentioning
confidence: 99%
“…14 ). 36 Relying on either direct or acetone-sensitized excitation, the desired azetidine ( 44 ) was isolated in 80–85% yield. Notably, the imine 43 used in this report did not require any conjugating group for successful reactivity.…”
Section: Scope and Limitationsmentioning
confidence: 99%
“…Excitation of the CN bond is known to lead to isomerization, rearrangement, hydrolysis, oxidation, photoreduction, and photoalkylation 1. Although olefins have been reported to undergo cycloaddition to photoexcited imines containing electron‐withdrawing groups on the nitrogen atom,1ac, 2 generally useful preparative examples of [2+2] photocycloadditions to CN bonds are very rare. Furthermore, the reverse situation in which the imine is the ground‐state partner during the cycloaddition with a photoexcited alkene has, to our knowledge, yet to be reported.…”
Section: Methodsmentioning
confidence: 99%