Free-radical rearrangements in the thermal decomposition of tert-butylperoxy 3-(1-phenylcyclopropyl)propanoate, 4-(1-phenylcyclopropyl)butanoate, and 5-(1-phenylcyclopropyl)pentanoate

Doyle, Michael P.; Raynolds, Peter W.; Barents, Rosalyn A.; Bade, Thomas R.; Danen, Wayne C.; West, Charles T.

doi:10.1021/ja00799a028

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1973

1980

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Cited by 17 publications

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“…However, a few examples of the formation of dihydroarenes are known, e.g., 165 -> 166 (119). However, a few examples of the formation of dihydroarenes are known, e.g., 165 -> 166 (119).…”

mentioning

confidence: 99%

Free-Radical Rearrangements

Beckwith¹,

Ingold²

1980

Organic Chemistry: A Series of Monographs

114

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“…However, a few examples of the formation of dihydroarenes are known, e.g., 165 -> 166 (119). However, a few examples of the formation of dihydroarenes are known, e.g., 165 -> 166 (119).…”

mentioning

confidence: 99%

Free-Radical Rearrangements

Beckwith¹,

Ingold²

1980

Organic Chemistry: A Series of Monographs

114

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Offene und verbrückte Zwischenstufen, 8. Zur Norbornenyl‐Nortricyclyl‐Radikalumlagerung

Giese

Jay

1977

Chem. Ber.

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Bei der radikalischen Addition von BrCCl, und CC14 an Norbornadien wird eine starke Abhangigkeit der Produktzusammensetzung 7: 9 + 10 von der Reaktionstemperatur und der XCCI,-Konzentration beobachtet. So Open and Bridged Intermediates, 8')The Norbornenyl-Nortricyclyl RearrangementIn the radical addition of BrCC1, and CC1, to norbornadiene the product ratio 7:9 + 10 shows a considerable dependency on the reaction temperature. At 1OO'C the nortricyclyl derivatives 9a + 10a predominate with 81% in BrCCI,, whereas at 0°C the norbornenyl adduct 7 a is the main product (64%). A change in the BrCCI, concentration from 9.69 mol/htre to 0.95 mol/litre causes the product ratio 7a:9a + 10a to change from 64:36 to 21:79. Kinetic measurements using the rate equation (f) at temperatures between 0 and 100°C yield the differences in the activation parameters between the halogen abstraction 6 + 7 and 8 + 9 + 10 respectively and the norbornenylnortricyclyl rearrangement 6 + 8. The activation enthalpies of the bromine abstraction from BrCCl, are 4.4 [kcal/mol] (6 + 7a) and 2.1 [kcal/mol] (8 + 9a + 10a) respectively smaller than the activation enthalpies of the norbornenyl-nortricyclyl rearrangement 6 8 (table 1, figure 3), whereas the activation enthalpies of the chlorine abstraction from CC14 are 5.6 [kcal/mol] (6 + 7b) and 3.8 [kcal/mol] (8 + 9b + lob) respectively higher than the activation enthalpies of the rearrangement 6 s 8 (table 2, figure 3).Das Auftreten von verbruckten, nicht-klassischen Ionen 2 haben wir kiirzlich bei der Halogenierung, Protonierung und Mercurierung der Olefine 1 wahrscheinlich gemacht ' ;.

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