Conformation et reactivite de derives (4.n.0) bicycliques a jonction trans—XXVII

Laureillard, J.; Casadevall, A.

doi:10.1016/0040-4020(80)80007-x

Cited by 3 publications

(2 citation statements)

References 36 publications

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“…The identification of these products was performed by VPC and 'H-NMR comparisons with authentical samples. Olefins were obtained as reported in [I I] and [7].…”

Section: Experimental Partmentioning

confidence: 99%

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Parallelism Between Nucleophilically Solvent‐Assisted and Phenyl‐Assisted Reactions. Possible Existence of Nucleophilically β‐Phenyl‐Solvated Ion Pairs

Laureillard¹,

Casadevall²

1984

Helvetica Chimica Acta

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Solvolysis rate constants in MeOH and t‐BuOh are compared for β‐methyl and β‐phenyl derivatives of two cycloakyl systems. It appears that the β‐phenyl derivatives solvolyse at te same rate as the β‐methyl ones. The lack of deceleration is attributed to phenyl assistance. It is established by configurational analysis of the reaction products, that those products which necessarily originate from a cationic species are the most abundant ones. It is suggested that these reactions could proceed through ion‐pair intermediates, which are nucleophilically solvated by phelyl or by the solvent. A parallel between phenyl assistance and ‘SN2 (intermediate)’ mechanism, suggested by Bentely & Schleyer, is drawn.

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“…The identification of these products was performed by VPC and 'H-NMR comparisons with authentical samples. Olefins were obtained as reported in [I I] and [7].…”

Section: Experimental Partmentioning

confidence: 99%

“…For these compounds, the nomenclature previously used in [7] was adopted. Diaxial compounds always react in chair form, but the reactions of the diequatorial ones can still proceed vio non-chair conformations.…”

Section: Surnnzarymentioning

confidence: 99%

Parallelism Between Nucleophilically Solvent‐Assisted and Phenyl‐Assisted Reactions. Possible Existence of Nucleophilically β‐Phenyl‐Solvated Ion Pairs

Laureillard¹,

Casadevall²

1984

Helvetica Chimica Acta

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Assistance d'un groupe voisin pour des tosylates secondaires β substitues diequatoriaux dans l'hexafluoroisopropanol 97%

Laureillard

1984

Tetrahedron

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Mise en evidence du mecanisme “s2 (intermediaire)” dans des solvolyses de tosylates secondaires encombres. absence de correspondance vitesses-produits

Laureillard¹,

Casadevall²

1984

Tetrahedron

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Conformation et reactivite de derives (4.n.0) bicycliques a jonction trans—XXVII

Cited by 3 publications

References 36 publications

Parallelism Between Nucleophilically Solvent‐Assisted and Phenyl‐Assisted Reactions. Possible Existence of Nucleophilically β‐Phenyl‐Solvated Ion Pairs

Parallelism Between Nucleophilically Solvent‐Assisted and Phenyl‐Assisted Reactions. Possible Existence of Nucleophilically β‐Phenyl‐Solvated Ion Pairs

Assistance d'un groupe voisin pour des tosylates secondaires β substitues diequatoriaux dans l'hexafluoroisopropanol 97%

Mise en evidence du mecanisme “s2 (intermediaire)” dans des solvolyses de tosylates secondaires encombres. absence de correspondance vitesses-produits

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