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CF₃-Containing para-Quinone Methides for Organic Synthesis.

ABSTRACT: A new family of CF₃-containing para-quinone methides (CF₃-QMs) was systematically investigated for its suitability in organic synthesis. Addition of different nucleophiles gives access to target molecules with a benzylic CF₃-containing stereogenic center straightforwardly. The electrophilicity parameter E of the prototypical CF₃-QM 2,6-di-tert-butyl-4-(2,2,2-trifluoroethylidene)cyclohexa-2,5-dien-1-one was determined to be -11.68 according to the Mayr scale, making it one of the most reactive quinone methides known so far.

SUBMITTER: Winter M

PROVIDER: S-EPMC7335660 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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CF3-Containing para-Quinone Methides for Organic Synthesis.

Winter Michael M Schütz Roman R Eitzinger Andreas A Ofial Armin R AR Waser Mario M

European journal of organic chemistry 20200306 25

A new family of CF3-containing para-quinone methides (CF3-QMs) was systematically investigated for its suitability in organic synthesis. Addition of different nucleophiles gives access to target molecules with a benzylic CF3-containing stereogenic center straightforwardly. The electrophilicity parameter E of the prototypical CF3-QM 2,6-di-tert-butyl-4-(2,2,2-trifluoroethylidene)cyclohexa-2,5-dien-1-one was determined to be -11.68 a ...[more]

PMID: 32624681

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