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Nucleophilic addition to C,C double bonds. III. Chemical reactivity of 1endo, 4endo: 5exo, 8exo-dimethano-1,2,3,4,4a,5,8,8a-octahydronaphthalen-10syn-ol and X-ray structure analysis of its p-nitrobenzoate

✍ Scribed by Rolland A. Pfund; W. Bernd Schweizer; Camille Ganter

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
400 KB
Volume
63
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 10‐methyl analogue 2. This forms the corresponding ether 7 at a much higher rate. ‐ In a deuteriated medium, base‐catalysed cyclization of 1 gives the exo‐deuteriated ether 6, corresponding to trans‐addition. ‐ An X‐ray structure analysis of 4, the p‐nitrobenzoate of 1, is presented.

📜 SIMILAR VOLUMES

Nucleophilic Addition to C,C-Double Bond
Nucleophilic Addition to C,C-Double Bonds. Part VIII. The standard enthalpies of formation of anti9,10-10endo-hydroxytricyclo [4.2.1.12,5]deca-3,7-dien-9-one and 9-Oxatetracyclo [5.4.0.03,10.04,8]undec-5-en-2-one and kinetic data for the cyclization of the olefinic alcohol to the ether
✍ Alan A. Smeaton; William V. Steele; Gerardo M. Ramos Tombo; Camille Ganter 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 258 KB 👁 2 views

## Abstract In view of the significance of steric compression in the base‐catalyzed intramolecular cyclization of polycyclic olefinic alcohols, the standard enthalpies of formation of __anti__^9,10^‐10 __endo__‐hydroxytricyclo [4.2.1.1^2,5^]deca‐3,7‐dien‐9‐one **(1)** and 9‐oxatetracyclo [5.4.0.0^3