Graduate Thesis Or Dissertation
 

Oxymercuration of cyclodeca-1,2,5,8-tetraene

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  • The reactions of cyclodeca-1, 2, 5, 8-tetraene with mercuric salts in solvents of varying nucleophilicity are described. Instead of forming the usual oxymercuration products reported for reactions of olefins and allenes with mercuric salts, the major products obtained in the present cases result from the initial electrophilic addition of the mercuric salt to the central carbon of the allenic unit forming a mercurinium ion, followed by a transannular attack at the olefinic bonds via a delocalized ion intermediate. Under all conditions, the oxymercuration reaction stereospecifically gives cis-syn-1, 2, 5, 8, 4a, 8ahexahydronaphthalen- l-ol as a predominant product, and the amounts formed are found to be in direct relation to the nucleophilicity of the solvents. A significant amount (54%) of tricyclo[4. 4. 0. 0²'⁴]deca-5, 8- diene is formed when acetic acid is used as a solvent.
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