Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue -, Pages 2531-2538Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.10.264
Keywords
BHT; dehydrohalogenation/rearrangement; Friedel-Crafts acylation; methylenenortricyclene; superoxide ion
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Funding
- CSIR-India
- CSIR
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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.
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