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Polar versus steric effects in the solvolysis of 6endo-substituted 2endo-norbornyl p-toluenesulfonates. Norbornanes, Part 8

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

Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
337 KB
Volume
65
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 therefore concluded that polar rather than steric effects control the exo/endo‐rate ratios of norbornyl sulfonates. Products are derived mainly from rearranged 6__exo__‐R‐norbornyl cations when the substituent is an electron donor and from unrearranged 6__endo__‐R‐substituted cations when the substituent is an electron acceptor.

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✍ Cyril A. Grob; Bettina Günther; Reinhard Hanreich 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 German ⚖ 471 KB

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