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C,C-Double Bond Participation in the Acid-Catalyzed Cyclization of 9exo-Methyl-anti10,11-tricyclo[4.2.1.12,5]deca-3,7-diene-9endo, 10endo-diol. Influence of Steric Compression on the Product Distribution

✍ Scribed by Gerardo M. Ramos Tombo; Sarmistha Chakrabarti; Camille Ganter

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
408 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Acid treatment of 9__exo__‐methyl‐anti^10,11^‐tricyclo[4.2.1.1^2,5^]deca‐3,7‐diene‐9__endo__, 10__endo__‐diol (8) leads to the two isomeric pentacyclic ethers 7 and 9 by intramolecular nucleophilic substitution of a protonated OH‐group with participation of a C,C‐double bond.

The higher steric compression in diol 8 on the side of the tertiary OH‐group at C(9) and the C(3), C(4)‐double bond, accounts for the preferred formation of 7 over 9.

📜 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