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Volumn 2, Issue 4, 2004, Pages 455-465

Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; CATALYSIS; CHEMICAL ACTIVATION; FLUORINE; FURAN RESINS; KETONES; SYNTHESIS (CHEMICAL);

EID: 1342344957     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b314314g     Document Type: Article
Times cited : (17)

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    • S. Y. Wang and W. T. Borden, J. Am. Chem. Soc., 1989, 111, 72827283; S. J. Getty and W. T. Borden, J. Am. Chem. Soc., 1991, 113, 4334-4335. Borden shows that the low reactivity of tetrafluoroethylene in [4 + 2] cycloaddition reactions arises from the facility with which it undergoes [2 + 2] cycloadditions via biradical pathways. Alkene ground state destabilisation and biradical stabilisation contribute to the effect.
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    • note
    • Reference 20b reviews related Brønsted and Lewis acid-mediated ring openings of the oxabicyclo[2.2.1]heptenyl template.
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    • Many of the literature examples take place upon symmetrical systems so electronic influences upon the hydrostannylation reaction have not been defined. For an attempt to detect such influences upon carbopalladtion reactions of the oxabicyclo[2.2.1]heptenyl template, see : C. Montalbetti, M. Savignac, J.-P. Gênet, J.-M. Roulet and P. Vogel, Tetrahedron Lett., 1996, 37, 2225-2228.
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