The Reaction of N-Bromosuccinimide with Cycloheptatriene<sup>1</sup>

Dryden, Hugh L.; Burgert, B.E.

doi:10.1021/ja01626a050

Cited by 20 publications

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“…1985, 105, 1. (10) The values of c¡ and C! are in good agreement with those reported by Francois et al7 *These authors reported that ct and c1 are independent of the molecular weight of the polymer in the range of 6,000-200,000.…”

Section: Resultsmentioning

confidence: 99%

Perturbation of SDS and CTAB micelles by complexation with poly(ethylene oxide) and poly(propylene oxide)

Witte¹,

Engberts²

1987

J. Org. Chem.

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Pseudo-first-order rate constants have been determined for the neutral hydrolysis of l-benzoyl-3-phenyl-1,2,4-triazole in aqueous solutions in the presence of SDS and CTAB micelles and SDS-PEO, SDS-PPO, and CTAB-PPO mixed micelles. The micellar rate inhibition of the hydrolysis is clearly modified as a result of micelle-polymer complexation, the effects being rather specific for the nature of the surfactant and the polymer. The kinetic data were analyzed by a simple pseudophase model. The results revealed stabilization of the micelles by interaction with the polymer and polymer-induced microenvironmental changes at the micellar binding sites of the substrate. Results from conductivity measurements facilitated the interpretation of the kinetic data.

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Section: Resultsmentioning

confidence: 99%

Perturbation of SDS and CTAB micelles by complexation with poly(ethylene oxide) and poly(propylene oxide)

Witte¹,

Engberts²

1987

J. Org. Chem.

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“…For example, the reaction of dimethylketene with trans -1-methoxybutadiene ( 5 ) gives the corresponding cyclobutanone, 2,2-dimethyl-3-( trans -2‘-methoxyvinyl)cyclobutan-1-one 29a. Also, reactions between diphenylketene ( 1 ) with butadienes (butadiene, 11d, trans -1-acetoxy-butadiene, cis -1-cyanobutadiene, , trans -1-methylbutadiene, 9a,, cis -1-methylbutadiene, ,34b and 2-methylbutadiene, 11d,,34b etc.) afford cyclobutanones.…”

Section: Referencesmentioning

confidence: 99%

“…In the first decades of this century, Staudinger discovered ketene − and its reactions in the cycloaddition of diphenylketene 2 ( 1 ) and cyclopentadiene ( 2 ). − The pioneering studies on ketene [2 + 2] cycloadditions (Staudinger reactions) have been confirmed by a huge number of experiments. − They showed that ketenes react with olefins across the C  C bond rather than the C  O one . Ketenes are potentially useful dienophiles but they do not appear to owe their reactivity toward dienes to Diels−Alder reactions.…”

Section: Introductionmentioning

confidence: 99%

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Ketene Recognizes 1,3-Dienes in Their s-Cis Forms through [4 + 2] (Diels−Alder) and [2 + 2] (Staudinger) Reactions. An Innovation of Ketene Chemistry

et al. 1999

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The mechanism of ketene-diene reactions has been studied both experimentally and theoretically. Careful experiments of the reactions of diphenylketene (1) with cyclic (s-cis) 1,3-dienes [cyclopentadiene (2) and cyclohexa-1,3-diene (3)] lead to the first direct detection of the Diels-Alder cycloadducts (10 and 11) by low-temperature NMR spectroscopy. The initially formed cycloadducts are converted to the final Staudinger products, cyclobutanones (6 and 7), by [3,3] sigmatropic (Claisen) rearrangements. In contrast, ketene 1 reacts with open-chain 1,3-dienes [2,3-dimethyl-1,3-butadiene (4) and 1-methoxy-1,3-butadiene ( 5)] to afford initially both the Staudinger-type (8, 9) and Diels-Alder-type cycloadducts (12, 13). The Staudinger cycloadducts (8, 9) are converted eventually to Diels-Alder products (12, 13) by the retro-Claisen rearrangement. Thus, ketene recognizes dienes in cycloadditions as ketenophiles different from olefins. [4 + 2] and [2 + 2] cycloadducts are generated and can be intermediates or products flexibly according to diene structures.

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Das Tropylium‐Ion

Doering

Krauch

1956

Angewandte Chemie

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The Reaction of N-Bromosuccinimide with Cycloheptatriene¹

Cited by 20 publications

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Perturbation of SDS and CTAB micelles by complexation with poly(ethylene oxide) and poly(propylene oxide)

Perturbation of SDS and CTAB micelles by complexation with poly(ethylene oxide) and poly(propylene oxide)

Ketene Recognizes 1,3-Dienes in Their s-Cis Forms through [4 + 2] (Diels−Alder) and [2 + 2] (Staudinger) Reactions. An Innovation of Ketene Chemistry

Das Tropylium‐Ion

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The Reaction of N-Bromosuccinimide with Cycloheptatriene1

Cited by 20 publications

References 0 publications

Perturbation of SDS and CTAB micelles by complexation with poly(ethylene oxide) and poly(propylene oxide)

Perturbation of SDS and CTAB micelles by complexation with poly(ethylene oxide) and poly(propylene oxide)

Ketene Recognizes 1,3-Dienes in Their s-Cis Forms through [4 + 2] (Diels−Alder) and [2 + 2] (Staudinger) Reactions. An Innovation of Ketene Chemistry

Das Tropylium‐Ion

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The Reaction of N-Bromosuccinimide with Cycloheptatriene¹