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Polar and anchimeric effects in the solvolysis of 6-endo-substituted 2-norbornyl-p-toluene-sulfonates

✍ Scribed by Cyril A. Grob; Bettina Gunther; Reinhard Hanreich

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
192 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

A study of the influence of 6-endo substituents on the reactivity of 2-exoand 2-endo-norbornyl p-toluenesulfonates 3 and 4, respectively, confirms that polar rather than steric effects control relative rates.

📜 SIMILAR VOLUMES

Polar versus steric effects in the solvo
Polar versus steric effects in the solvolysis of 6endo-substituted 2endo-norbornyl p-toluenesulfonates. Norbornanes, Part 8
✍ Cyril A. Grob; Bettina Günther; Reinhard Hanreich 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 German ⚖ 337 KB 👁 1 views

## Abstract The solvolysis rates and products of the 6__endo__‐R‐substituted 2__endo__‐norbornyl toluenesulfonates **6a**–**6i** have been determined. The rates of **6a**–**6g** correlate with the inductive constants σ the 6__endo__‐substituents and are not related to the size of the latter. It is

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-endo-Substituted 2-exo-Norbornyl Toluenesulfonates. Norbornanes part 6
✍ Cyril A. Grob; Bettina Günther; Reinhard Hanreich 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 German ⚖ 471 KB 👁 1 views

## Abstract The solvolysis rate constants __k__ for the 6‐__endo__‐substituted 2‐__exo__‐norbornyl toluenesulfonates **7** have been determined. Values of log__k__ correlate well with the respective inductive constants of the substitutents except when the latter are nucleophilic and therefore lead

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