Superoxide chemistry revisited: synthesis of tetrachloro-substituted methylenenortricyclenes

Budanur, B M and Khan, Faiz Ahmed (2014) Superoxide chemistry revisited: synthesis of tetrachloro-substituted methylenenortricyclenes. Beilstein Journal of Organic Chemistry, 10. pp. 2531-2538. ISSN 1860-5397

Preview

PDF (Open access) BJ-org-Chem_2014_10_2531-2538.pdf - Published Version Download (556kB)

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-d6. Friedel-Crafts acylation reactions of 3-methylenenorticyclenes yielded 2-propanone-substituted pentachloronorbornenes.

[error in script]

IITH Creators:	IITH Creators ORCiD Khan, Faiz Ahmed UNSPECIFIED
Item Type:	Article
Uncontrolled Keywords:	BHT; Dehydrohalogenation/rearrangement; Friedel-Crafts acylation; Methylenenortricyclene; Superoxide ion
Subjects:	?? sub5.8 ??
Divisions:	Department of Chemistry
Depositing User:	Team Library
Date Deposited:	12 Jan 2015 05:56
Last Modified:	21 Sep 2017 06:54
URI:	http://raiithold.iith.ac.in/id/eprint/1315
Publisher URL:	https://doi.org/10.3762/bjoc.10.264/
OA policy:	http://www.sherpa.ac.uk/romeo/issn/1860-5397/
Related URLs:	Google Scholar

Actions (login required)

View Item

Statistics for this ePrint Item