Electrophilic Substitution with Allylic Rearrangement (SE′). Anti Stereoselectivity in Trifluoroacetolysis of Some CycIohex-2-enylsilanes, -germanes, and -stannanes

Journal of Organic Chemistry

Volumn 48, Issue 4, 1983, Pages 612-614

  Wickham, Geoffrey ^a   Kitching, William ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009955838     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00152a044     Document Type: Letter

References (25)

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2. Negishi, E. I. “Organometallics in Organic Synthesis”; Wiley: New York, 1980; Vol. 1.
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4. For a review see: Mangravite, J. A. Organomet. Chem. Rev. 1979, 7, 45.
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11. For kinetic information on protodemetalations of allylic systems see: Verdone, J. A.; Mangravite, J. A.; Scarpa, N. M.; Kuivila, H. G. J. Am. Chem. Soc. 1975, 97, 843.
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13. Although a fully concerted mechanism would exhibit stereospecificity, second-order kinetics does not distinguish between such a mechanism and others involving the slow or reversible formation of an intermediate. See also: Fleming, I.; Langley, J. A. J. Chem. Soc, Perkin Trans. 1 1981,1421.
14. Fleming, I.; Marchi, D.; Patel, S. K. J. Chem. Soc, Perkin Trans. 1 1981, 2518.
15. For example see: Au-Yeung, B. W.; Fleming, I. J. Chem. Soc, Chem. Commun. 1977, 79.
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25. Wickham, G. Ph.D. Thesis, University of Queensland, 1983.