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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 8, 1978 - Issue 1
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Original Articles

Organometallic Compounds with Cage Structures: 1-Adamantyl Lithium

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Pages 39-43 | Received 06 Oct 1977, Published online: 06 Dec 2006

References

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  • Personal communication by P.v.R. Schleyer, cited in 11
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  • Dubois , J. E. , Bauer , P. , Molle , G. and Daza , J. 1977 . Compt. rend. , 284C : 145 In contrast with 1‐bromoadamantane, under these same conditions deuterolysis of the final solution yields 18% deuterated adamantane, 26% l,l‐diadamantane, 5% l‐adamantanol and 51% non deuterated adamantane. However l‐Adamantyl magnesium bromide was also synthesized directly for the first time with a yield of about 60%
  • Hold , T. and Crossland , I. 1971 . Acta Chem. Scand. , 24 : 59 The tertiobutylmagnesium chloride reaction on benzophenone also leads to substitution products on the aromatic nucleus of the ketone
  • It is apparent that alcohol III, formed in the medium, reacts competitively with l‐AdLi and complex V. These reactions, which limit the yield of alcohol III probably explain the presence of non‐deuterated adamantane in the products after deuterolysis

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