Fragmentation of carbohydrate anomeric alkoxy radicals: A new synthesis of chiral 1-halo-1-iodo compounds

Gonzalez, C.C. and Kennedy, A.R. and Leon, E.I. and Riesco-Fagundo, C. and Suarez, E. (2001) Fragmentation of carbohydrate anomeric alkoxy radicals: A new synthesis of chiral 1-halo-1-iodo compounds. Angewandte Chemie, 40 (12). pp. 2326-2331. ISSN 1521-3773 (http://dx.doi.org/10.1002/1521-3773)

Abstract

The reaction of 1,2-halohydrins derived from easily available carbohydrates with (diacetoxyiodo)benzene (DIB) in the presence of bromine is a mild procedure for the synthesis of 1-deoxy-1-halo-1-bromo-alditols with one carbon less than the original carbohydrate. The reaction goes through β-fragmentation of the intermediate anomeric alkoxyl radicals. These 1-halo-1-bromo polyhydroxy compounds may be valuable synthetic intermediates in organic synthesis.

ORCID iDs

Kennedy, A.R. ORCID: https://orcid.org/0000-0003-3652-6015

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• Item metadata

  Item type:	Article
  ID code:	1242
  Dates:	Date Event 18 June 2001 Published
  Notes:	Related item: http://strathprints.strath.ac.uk/22673/ Non-duplicate
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry Faculty of Engineering > Electronic and Electrical Engineering
  Depositing user:	Users 45 not found.
  Date deposited:	12 Jun 2006
  Last modified:	29 Jan 2025 17:36
  Related URLs:	Strathprints record
  URI:	https://strathprints.strath.ac.uk/id/eprint/1242