Reactions of Alkynyldihaloboranes with 1,3-Dienes. 1,4-Alkynylborations and Stepwise Diels-Alder Reactions

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 1955-1960

  Leung, Shun Wang ^a   Singleton, Daniel A ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000367234     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961892h     Document Type: Article

References (26)

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3. Singleton, D. A.; Martinez, J. P.; Watson, J. V.; Ndip, G. M Tetrahedron 1992, 48, 5831. Singleton. D. A.; Kim, K.; Martinez, J. P. Tetrahedron Lett. 1993, 34, 3071.
4. Singleton, D. A.; Martinez, J. P.; Watson, J. V.; Ndip, G. M Tetrahedron 1992, 48, 5831. Singleton. D. A.; Kim, K.; Martinez, J. P. Tetrahedron Lett. 1993, 34, 3071.
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8. A complication caused by the use of protodeboronation was that in some cases (10-13, 20, 26, 27) the nonpolar products could not be completely separated from nonpolar impurities. NMR spectra of these materials, as isolated, are given in the Supporting Information.
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10. If just acetic acid is used, HCl is generated and the yields are low. The combination of triethylamine with acetic acid appears particularly effective in the protodeboronation of alkenyldichloroboranes.
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14. E = -1174.867 487. Structure 31 is fully optimized and exhibited one imaginary frequency. The predicted activation energy is 31.55 kcal/mol.
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