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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 9
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Original Articles

A Short Synthesis of Symmetrical Betweenanemes

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Pages 689-692 | Published online: 06 Dec 2006

References

  • Marshall , J. A. and Lewellyn , M. E. 1977 . J. Am. Chem. Soc. , 99 : 3508 J. A. Marshall and K-H. Chung, J. Org. Chem. 44, 1566 (1979)
  • Ziegler , K. and Aurnhammer , R. 1934 . Ann. , 513 : 43
  • Leonard , N. J. and Schimelpfenig , C. W. Jr. 1958 . J. Org. Chem. , 23 : 1708
  • Blomquist , A. T. , Prager , J. and Wolinsky , J. 1955 . J. Am. Chem. Soc. , 77 : 1804
  • McMurry , J. E. , Fleming , M. P. , Kees , K. L. and Krepski , L. R. 1978 . J. Org. Chem. , 43 : 3255
  • Nakazaki , M. , Yamamoto , K. and Yanagi , J. 1979 . J. Am. Chem. Soc. , 101 : 147
  • Bierenbaum , R. 1979 . Synthesis of Betweenanenes , PhD Thesis 115 Northwestern University . (Part II)
  • Added in “Proof”: We have recently effected the cyclodimerization of docosanedioyl chloride (1, a = 20) to dione 2 (a = 20) in 31% yield. Cyclization to the bicyclic alkene (31% yield) followed by irradiation yielded a 2.3:1 mixture of [20.20]betweenanene (4, a = 20) and recovered cis alkene 3 (a=20). It therefore appears that large ring symmetrical betweenanenes can be secured via this straightforward sequence

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