Attempted synthesis of the imidazylate of an α-hydroxylactone results in unexpected chlorination: Synthesis and X-ray crystal structure of 5-Chloro-5-deoxy-1,2- O -isopropylidene-β- l -idurono-6,3-lactone

Mohamed, Shifaza, Bernhardt, Paul V. and Ferro, Vito (2014) Attempted synthesis of the imidazylate of an α-hydroxylactone results in unexpected chlorination: Synthesis and X-ray crystal structure of 5-Chloro-5-deoxy-1,2- O -isopropylidene-β- l -idurono-6,3-lactone. Journal of Carbohydrate Chemistry, 33 4: 197-205. doi:10.1080/07328303.2014.907908


Author Mohamed, Shifaza
Bernhardt, Paul V.
Ferro, Vito
Title Attempted synthesis of the imidazylate of an α-hydroxylactone results in unexpected chlorination: Synthesis and X-ray crystal structure of 5-Chloro-5-deoxy-1,2- O -isopropylidene-β- l -idurono-6,3-lactone
Journal name Journal of Carbohydrate Chemistry   Check publisher's open access policy
ISSN 1532-2327
0732-8303
Publication date 2014-05-04
Sub-type Article (original research)
DOI 10.1080/07328303.2014.907908
Volume 33
Issue 4
Start page 197
End page 205
Total pages 9
Place of publication Philadelphia, PA, United States
Publisher Taylor and Francis
Collection year 2015
Language eng
Abstract Attempted synthesis of the imidazylate derivative of 1,2-O-isopropylidene- α-D-glucurono-6,3-lactone (2) via treatment with sulfuryl chloride in the presence of excess imidazole in DMF at either -40°C or -70°C resulted in the unexpected formation of 5-chloro-5-deoxy-1,2-O-isopropylidene-β-l- idurono-6,3-lactone (7). Chloride 7 presumably forms via the rapid S N2 displacement by a chloride ion of an initially formed chlorosulfate ester intermediate, which is evidently unusually reactive. The identity of the product was confirmed by a single-crystal X-ray structure determination.
Keyword Chlorination
Idurono-6,3-lactone
X-ray crystal structure
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
School of Chemistry and Molecular Biosciences
 
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