The Acid-catalyzed Isomerization of the Adducts of Azodiacyls with Cyclopentadiene and 1,3-Cyclohexadiene

Chung, Miss C. Y-J.; Mackay, Donald; Sauer, Tim

doi:10.1139/v72-248

Cited by 9 publications

(1 citation statement)

References 11 publications

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“…(4), Scheme 1]. [7] More recently, the corresponding protic or Lewis acid-catalyzed (LA) rearrangement of carbobenzyloxy-protected bicyclic [2.2.1] hydrazine 1a was explained by means of a transient allylic cation to give 5,6-bicyclic . [4,5b] As compound 4a has an allylic leaving group, we considered this compound as a possible candidate for an allylic alkylation with Grignard reagents.…”

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confidence: 99%

Sequential Copper‐Catalyzed Rearrangement–Allylic Substitution of Bicyclic Hydrazines with Grignard Reagents

et al. 2009

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The problem of the synthesis of trans-1,4-disubstituted hydrazino and amino cyclopentenes has been resolved by a sequential copper-catalyzed rearrangement-allylic alkylation of 2,3-diazabicyclo[2.2.1]heptenes. The cis-fused 5,5-membered allylic carbazate which is formed in situ by a novel Cu(OTf)2/(±)-binap catalyzed rearrangement, can be alkylated with a broad spectrum of Grignard reagents with a predominant SN2’-regioselectivity. N-Boc protecting group proved to be optimal as regards yields, reaction times and regioselectivitie

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confidence: 99%

Sequential Copper‐Catalyzed Rearrangement–Allylic Substitution of Bicyclic Hydrazines with Grignard Reagents

et al. 2009

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Combining the Diaza‐Diels–Alder Reaction and Palladium‐Catalyzed Aminations to Prepare Amino‐Substituted Porphyrins

et al. 2014

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A strategy to tackle the synthesis of azoporphyrins with unsubstituted terminal meso positions was investigated. It comprised the combination of diaza‐Diels–Alder (DADA) reaction of 1,3‐dienes with dialkyl azodicarboxylates, decarboxylative hydrolysis of the bis(carbamates), palladium‐catalyzed amination of bromoporphyrin precursors, and retro‐DADA reactions to release the ultimate targets. The somewhat confused historical results on the DADA reactions of 1,3‐cyclohexadiene were clarified, but the hydrolyses yielded extremely air‐sensitive amines which decomposed completely in minutes via autooxidation and retro‐DADA reaction. With anthracene or 2,3‐dimethyl‐1,3‐butadiene as the diene, the synthesis of azoporphyrin was not achieved but three amino‐substituted porphyrins were obtained in moderate yields under mild conditions. The X‐ray crystal structures of several of the intermediates and the final aminoanthracene‐porphyrin nickel(II) complex were determined.

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ChemInform Abstract: SAEURE‐KATALYSIERTE ISOMERISIERUNG DER ADDUKTE VON AZODIACYLEN MIT CYCLOPENTADIEN UND CYCLOHEXADIEN‐(1,3)

Chung¹,

Mackay²,

Sauer³

1972

Chemischer Informationsdienst

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The Acid-catalyzed Isomerization of the Adducts of Azodiacyls with Cyclopentadiene and 1,3-Cyclohexadiene

Cited by 9 publications

References 11 publications

Sequential Copper‐Catalyzed Rearrangement–Allylic Substitution of Bicyclic Hydrazines with Grignard Reagents

Sequential Copper‐Catalyzed Rearrangement–Allylic Substitution of Bicyclic Hydrazines with Grignard Reagents

Combining the Diaza‐Diels–Alder Reaction and Palladium‐Catalyzed Aminations to Prepare Amino‐Substituted Porphyrins

ChemInform Abstract: SAEURE‐KATALYSIERTE ISOMERISIERUNG DER ADDUKTE VON AZODIACYLEN MIT CYCLOPENTADIEN UND CYCLOHEXADIEN‐(1,3)

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