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Nucleophilic Reactivity of the Carbon-Carbon Double Bond. III. A Comparison of the Solvolytic Behavior of 5-Hexenyl and Cyclopentylcarbinyl p-Nitrobenzenesulfonates 1

✍ Scribed by Bartlett, Paul D.; Closson, William D.; Cogdell, Thomas J.

Book ID: 127070400
Publisher: American Chemical Society
Year: 1965
Tongue: English
Weight: 846 KB
Volume: 87
Category: Article
ISSN: 0002-7863
DOI: 10.1021/ja01084a027

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## Abstract The title compound **1** is a further example of an olefinic alcohol that undergoes ether formation under basic conditions **(→ 3)** although the double bond is not activated by an electron‐attracting group. This unusual reactivity is due to steric compression, which is increased in the