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Superoxide chemistry revisited: synthesis of tetrachloro-substituted methylenenortricyclenes.


ABSTRACT: An unexpected reactivity of the superoxide ion leading to the synthesis of tetrachloroaryl/vinyl-substituted nortricyclenes through its dual mode of action has been reported. KO2 was found to be superior and the only reagent to perform this kind of reaction over other conventional bases. Addition of the antioxidant BHT (2,6-di-tert-butyl-4-methylphenol) improved the yields of methylenenortricyclenes. A complete deuterium incorporation was observed in the superoxide-mediated reaction in DMSO-d 6. Friedel-Crafts acylation reactions of 3-methylenenorticyclenes yielded 2-propanone-substituted pentachloronorbornenes.

SUBMITTER: Budanur BM 

PROVIDER: S-EPMC4222393 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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Superoxide chemistry revisited: synthesis of tetrachloro-substituted methylenenortricyclenes.

Budanur Basavaraj M BM   Khan Faiz Ahmed FA  

Beilstein journal of organic chemistry 20141030


An unexpected reactivity of the superoxide ion leading to the synthesis of tetrachloroaryl/vinyl-substituted nortricyclenes through its dual mode of action has been reported. KO2 was found to be superior and the only reagent to perform this kind of reaction over other conventional bases. Addition of the antioxidant BHT (2,6-di-tert-butyl-4-methylphenol) improved the yields of methylenenortricyclenes. A complete deuterium incorporation was observed in the superoxide-mediated reaction in DMSO-d 6.  ...[more]

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