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Inductive charge dispersal in the solvolysis of 2-exo- and 2-endo-norbornyl toluenesulfonates.

✍ Scribed by Francesco Fuso; Cyril A. Grob; Pawel Sawlewicz; Yao Guo-Wei

Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 197 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)98624-6

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✦ Synopsis

The effect of substituents at C4, 5, 6 and 7 on solvolysis rates and products of 2-exo-and 2-endo-norbornyl tosylates confirms that differential carbon participation is responsible for varying exo/endo rate and product ratios.

📜 SIMILAR VOLUMES

Epimeric 2-norbornyl cations in the solv

Epimeric 2-norbornyl cations in the solvolysis of 6-exo- and 6-endo-substituted 2-exo-norbornyl p-toluenesulfonates

✍ Cyril A. Grob; Bettina Günther; Reinhard Hanreich; Adrian Waldner 📂 Article 📅 1981 🏛 Elsevier Science 🌐 French ⚖ 188 KB

Polar effects in the solvolysis of 6-exo

Polar effects in the solvolysis of 6-exo-substituted endo-2-norbornyl p-toluenesulfonates

✍ W. Fischer; C.A. Grob; G. von Sprecher; A. Waldner 📂 Article 📅 1979 🏛 Elsevier Science 🌐 French ⚖ 157 KB

Inductive, CC-hyperconjugative and frang

Inductive, CC-hyperconjugative and frangomeric effects in the solvolysis of 6-exo-substituted 2-exo-norbornyl p-toluenesulfonates

✍ W. Fischer; C.A. Grob; G. von Sprecher 📂 Article 📅 1979 🏛 Elsevier Science 🌐 French ⚖ 172 KB

Stereoelectronic control of exo/endo rat

Stereoelectronic control of exo/endo rate ratios in the solvolysis of 2-norbornyl p-toluenesulfonates

✍ W. Fischer; C.A. Grob; G. von Sprecher; A. Waldner 📂 Article 📅 1979 🏛 Elsevier Science 🌐 French ⚖ 189 KB

The variable exo/endo rate ratios observed in the solvolysis of 6-exosubstituted exo-and endo-2-norbornyl p-toluenesulfonates are due to differential transmission of polar effects in the transition state for ionization.

Differential bridging in the solvolysis

Differential bridging in the solvolysis of 6- and 7-substituted 2-exo and 2-endo-norbornyl p-toluenesulfonates

✍ Peter Flury; Cyril A. Grob 📂 Article 📅 1983 🏛 Elsevier Science 🌐 French ⚖ 204 KB

The large difference between the reaction constants p, for the solvolysis of the 6-exo-and 7-anti-substituted norbornyl tosylates 3 and 1, respectively, is further proof for the hypothesis that 2-norbornyl cations are anisotropic with regard to the transmission of polar effects and that through spac

Carbon Participation in the Solvolysis o

Carbon Participation in the Solvolysis of 6-exo-substituted 2-exo- and 2-endo-Norbornyl p-Toluenesulfonates. Norbornanes part 5

✍ Walter Fischer; Cyril A. Grob; Reinhard Hanreich; Georg von Sprecher; Adrian Wal 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 German ⚖ 680 KB

## Abstract The solvolysis rates and products of the 6‐__exo__‐substituted 2‐__exo__‐ **1a**‐**1u**, and 2‐__endo__‐norbornyl __p__‐toluenesulfonates **2a**‐**2u**, have been determined. In general, the rate constants for **1** and **2** (log __k__) correlate well with the inductive constants σ of