✦ LIBER ✦

Solvolytic reactions of bicyclo[3.1.0]hexane-6-methanol

✍ Scribed by Kenneth B. Wiberg; Arthur J. Ashe III

Publisher: Elsevier Science
Year: 1965
Tongue: French
Weight: 208 KB
Volume: 6
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)84090-9

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✦ Synopsis

In connection with our interest in the participation of bicyclobutonium type ions in solvolytic reactions, and more specifically in the solvolysis of bicyclo[2. 1. O]pentane-5-methanol derivatives, we have examined the reactions of the exe-and endo-bicyclo[3. l.O]hexane-6-methyl tosylates (I and II). The alcohols required for the preparation of I and II were obtained as shown below: ;553 No. 21 The reactian of cyclopentene with diazoacetic ester gave largely the exo-ester (exe/ endo = 4 : 1). The -0 alcohols formed by reduction of the ester could be se:>arated by gas chromatography and the one formed in smaller amount was found to be identical with that obtained in the sequence starting with norbornadiene. The tosylates were formed via the treatment of the corresponding alkoxidc: with E-toluenesulfonyl chloride: The rates of solvolysip and the product!3 formed are indicated below:

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