Stereochemistry of Additions to Norbornene and 7,7-Dimethylnorbornene. A New Interpretation of the Steric Influence of 7,7-Dimethyl Substituents on Reactions of the Norbornyl System

Journal of the American Chemical Society

Volumn 92, Issue 1, 1970, Pages 201-202

  Brown, Herbert C ^a   Kawakami, James H ^a,b  

^a PURDUE UNIVERSITY   (United States)

^b NATIONAL SCIENCE FOUNDATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 4444370904     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00704a035     Document Type: Letter

References (17)

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9. H. M. Bell, Ph.D. Thesis, Purdue University.
10. M. A. Muhs and F. T. Weiss, J. Am. Chem. Soc., 84, 4697 (1962). Among the large number of olefins examined, only trans-cyclooctene formed a more stable complex.
11. J. Chatt, Chem. Rev., 48, 7 (1951).
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13. Oxymercurations of 1,4,7,7-tetramethylnorbornene and syn-7-bromonorbornene also yield the exo-cis adduct: T. T. Tidwell and T. G. Traylor, J. Org. Chem., 33, 2614 (1968). The present results confirm the conclusion that the earlier observations must be general and not the result either of enhanced torsional effects in the 1,4,7,7 derivative or of coordination effects in the syn-7-bromo compound.
14. H. C. Brown, J. H. Kawakami, and S. Ikegami, J. Org. Chem., 89, 1525 (1967).
15. H. C. Brown and K.-T. Liu, J. Org. Chem., 89, 3900 (1967).
16. The addition of thiophenol to a mixture of apobornene and apocyclene at 80° under the influence of azobisisobutyronitrile also produces the exo isomer predominantly. However, the exo:endo ratio was not established : D. I. Davies and P. J. Rowley, J. Chem. Soc., 1832 (1968).
17. H. C. Brown and K.-T. Liu, J. Am. Chem. Soc., 92, 200 (1970).