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Nucleophilic Reactions at Tertiary Carbon. Part 3. σ- and π-routes to the 9-decalyl cation

✍ Scribed by Konrad B. Becker; André F. Boschung; Manfred Geisel; Cyril A. Grob

Publisher
John Wiley and Sons
Year
1973
Tongue
German
Weight
775 KB
Volume
56
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The generation of the 9‐decalyl cation by solvolysis of cis‐ and trans‐9‐decalyl chloride (1) has been reinvestigated. The results of product, rate and isomerization studies implicate stereoisomeric ion pairs as intermediates, as in the case of the solvolysis of other stereoisomeric tertiary chlorides (Parts 1 and 2).

On the other hand, both symmetrically and unsymmetrically solvated 9‐decalyl cations are indicated in the cyclization of 4‐(cyclohexen‐1‐yl)butyl tosylate. No evidence was obtained that conformational isomers of the 9‐decalyl cation play a role as product determining intermediates.

📜 SIMILAR VOLUMES

Nucleophilic Reactions at Tertiary Carbo
Nucleophilic Reactions at Tertiary Carbon. Part 2. σ- and π-routes to the 8-hydrindanyl cation
✍ Konrad B. Becker; André F. Boschung; Cyril A. Grob 📂 Article 📅 1973 🏛 John Wiley and Sons 🌐 German ⚖ 913 KB

## Abstract Stereoisomeric ion pairs are implicated as intermediates in the solvolysis of __cis__ and __trans__‐8‐hydrindanyl chloride **3**, whereas 4‐(cyclopenten‐1‐yl)butyl tosylate **5** appears to cyclize by way of an unsymmetrically solvated 8‐hydrindanyl cation. This follows from the solvoly

Nucleophilic Reactions at Tertiary Carbo
Nucleophilic Reactions at Tertiary Carbon. Part 1. The 1,2-dimethyl-1-cyclohexyl cation
✍ Konrad B. Becker; Cyril A. Grob 📂 Article 📅 1973 🏛 John Wiley and Sons 🌐 German ⚖ 636 KB

## Abstract Stereoisomeric ion pairs are implicated as intermediates in the solvolysis of __cis__ and __trans__‐1‐chloro‐1,2‐dimethylcyclohexane, __cis__‐**4** and __trans__‐**4**, respectively. This follows from the rates and products of these stereoisomeric tertiary chlorides in 80% ethanol and 5