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Structure of Diels-Alder adduct of phenylated germole and 1,4-epoxy-1,4-dihydronaphthalene revisited

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Abstract

High pressure synthesis of Diels-Alder adduct of 1,1-dimetyl-2,3,4,5-tetraphenylgermole and 6,7-dibromo-1,4-epoxy-1,4-dihydronaphthalene is described. The X-ray crystallography analysis of the so obtained adduct indicated that the adduct has exo,endo-structure in agreement with our earlier proposal for the stereochemistry of the structurally related germa analogue, 11,11-dimethyl-9,10-epoxy-1,4-germa-1,2,3,4-tetraphenyl-1,4,4a,9,9a,10-hexahydroanthracene based on NMR analysis.

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Scheme 2
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Acknowledgments

The authors acknowledge the Croatian Ministry of Science, Education and Sport for financial support (grants 0098056, 0098147 and 0119632).

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Correspondence to Mirjana Eckert-Maksić.

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Margetić, D., Prugovečki, B., Đilović, I. et al. Structure of Diels-Alder adduct of phenylated germole and 1,4-epoxy-1,4-dihydronaphthalene revisited. Struct Chem 17, 301–306 (2006). https://doi.org/10.1007/s11224-006-9036-y

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Keywords

  • Diels-Alder reaction
  • High pressure
  • X-ray analysis
  • Organometallic
  • DFT calculations