Synthesis of sterically hindered ortho-substituted tetraphenylethenes. Electronic effects in the McMurry olefination reaction

Organic Letters

Volumn 8, Issue 7, 2006, Pages 1491-1494

  Chung, Mee Kyung ^a   Qi, Guizhong ^a   Stryker, Jeffrey M ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

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Indexed keywords

EID: 33645938923     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060318h     Document Type: Article

References (21)

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8. 4, bis(ortho-tolyl)methanone gives a very low yield of tetrakis(2-methylphenyl)ethene (15%) along with tetrakis(2-methylphenyl)ethane (40%): (a) Willem, R.; Pepermans, H.; Hallenga, K.; Gielen, M.; Dams, R.; Giese, H. J. J. Org. Chem. 1983, 48, 1890-1898.
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13. Complete experimental procedures and characterization data are provided as Supporting Information.
14. 2, and reactive hydride: Aleandri, L. E.; Becke, S.; Bogdanivic, B.; Jones, D. J.; Rozière, J. J. Organomet. Chem. 1994, 472, 97-112.
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19. Control experiments conducted by adding tetrakis(5-tert-butyl-2- methoxyphenyl)ethene 2a to an active McMurry reduction of 2,2′- dimethoxybenzophenone 1b clearly indicate that overreduction product 3a does not arise from direct reduction of 2a.
20. 4 and Ti powder in DME: Sullivan. J. M. U.S. Patent 6307063, 2001.
21. The two benzophenone arene rings cannot simultaneously maintain planarity with the carbonyl functionality, a consequence of ortho-substituent peri-interactions and, presumably, four-electron repulsion of methoxy and carbonyl lone electron pairs.