Axial dissymmetry induced magnetic nonequivalence in the <sup>13</sup>C nuclear magnetic resonance spectra of allenes

Beaulieu, Pierre L.; Morisset, Veronique M.; Garratt, Dennis G.

doi:10.1139/v80-146

Cited by 4 publications

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Electrophilic Additions to Allenes. VIII. The Kinetics and Mechanism of the Addition of Benzenesulphenyl Chloride to Allenes

Beaulieu

Morrisset

Garratt

1985

Israel Journal of Chemistry

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The rates of addition of benzenefulphenyl chloride to 62 alkyl substituted allenes have been determined in methylene chloride solution at 24.5°C. The rates of addition span a range of 3.4 × 103 in reactivity. No correlation with the extended Taft equation or variations thereof was found when the rates of all 62 compounds were considered. Partitioned rate constants, wherein each term reflects the relative propensity for attack upon a given π orbital‐lobe of the allenic system, allows one to demonstrate the specific effect of placing an alkyl group in each of three stereochemically distinct positions. Of note is the observation that while the magnitude of the polar effect of an alkyl group changes with the stereochemical location, this magnitude is a constant for methyl, ethyl and isopropyl. The rates reported herein are interpreted in terms of rate‐limiting formation of alkylidenethiiranium ions.

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Electrophilic Additions to Allenes. VIII. The Kinetics and Mechanism of the Addition of Benzenesulphenyl Chloride to Allenes

Beaulieu

Morrisset

Garratt

1985

Israel Journal of Chemistry

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¹³C chemical shift non‐equivalence in methylene carbons of monosubstituted cyclohexanes

Itô¹,

Renaldo²,

Johnson³

et al. 1989

Magnetic Reson in Chemistry

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Monosubstituted cyclohexanes were synthesized by addition of a cyclohexyl radical to olefins bearing different substituents at the a-position. Six distinct methylene "C resonances were observed, indicating that the methylene carbons located at the 2 and 6 positions and at the 3 and 5 positions are not magnetically equivalent. This magnetic non-equivalence (anisochronism) observed in the monosubstituted cyclohexanes is due to the introduction of an asymmetric center fl to the prochiral C-1 ring carbon.

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Prostereoisomerism (prochirality)

Eliel

Topics in Current Chemistry

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Axial dissymmetry induced magnetic nonequivalence in the ¹³C nuclear magnetic resonance spectra of allenes

Cited by 4 publications

References 1 publication

Electrophilic Additions to Allenes. VIII. The Kinetics and Mechanism of the Addition of Benzenesulphenyl Chloride to Allenes

Electrophilic Additions to Allenes. VIII. The Kinetics and Mechanism of the Addition of Benzenesulphenyl Chloride to Allenes

¹³C chemical shift non‐equivalence in methylene carbons of monosubstituted cyclohexanes

Prostereoisomerism (prochirality)

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Axial dissymmetry induced magnetic nonequivalence in the 13C nuclear magnetic resonance spectra of allenes

Cited by 4 publications

References 1 publication

Electrophilic Additions to Allenes. VIII. The Kinetics and Mechanism of the Addition of Benzenesulphenyl Chloride to Allenes

Electrophilic Additions to Allenes. VIII. The Kinetics and Mechanism of the Addition of Benzenesulphenyl Chloride to Allenes

13C chemical shift non‐equivalence in methylene carbons of monosubstituted cyclohexanes

Prostereoisomerism (prochirality)

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Product

Resources

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Axial dissymmetry induced magnetic nonequivalence in the ¹³C nuclear magnetic resonance spectra of allenes

¹³C chemical shift non‐equivalence in methylene carbons of monosubstituted cyclohexanes