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Exclusive ring opening of gem-dihalo-1,2-cyclopropanated oxyglycal to oxepines in AgOAc

Dey, Supriya and Jayaraman, N (2014) Exclusive ring opening of gem-dihalo-1,2-cyclopropanated oxyglycal to oxepines in AgOAc. In: CARBOHYDRATE RESEARCH, 389 . pp. 66-71.

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Official URL: http://dx.doi.org/10.1016/j.carres.2014.01.023


Treatment of gem-dihalo-1,2-cyclopropanated D-oxyglycal with primary, secondary, and unsaturated alcohols, in the presence of AgOAc, leads to the formation of chloro-oxepines exclusively. Reaction of the resulting 2-chloro-oxepines with excess alcohol in the presence of AgOAc, do not promote further reactions. This result is in contrast to the reactions of D-glucal derived halo-oxepine with alcohols known previously that lead to the formation of furanoses as the major product under similar reaction conditions. Observation of this study consolidates the reactivity differences of gem-dihalo-1,2-cyclopropanated oxyglycals, as compared to gem-dihalo- 1,2-cyclopropanated glycals. (C) 2014 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to the ELSEVIER SCI LTD, THE BOULEVARD, ENGLAND
Keywords: Cyclopropanes; Glycals; Oxepines; Oxyglycals; Ring expansion; Septanosides
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 03 Jun 2014 08:35
Last Modified: 03 Jun 2014 08:35
URI: http://eprints.iisc.ac.in/id/eprint/49113

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