Attempted Synthesis of the Imidazylate of an a- Hydroxylactone Results in Unexpected Chlorination: Synthesis and X- Ray Crystal Structure of 5-Chloro-5-deoxy1,2-O-isopropylidene- beta-Lidurono-6,3-lactone

作者：Mohamed Shifaza; Bernhardt Paul V; Ferro Vito^*

来源：Journal of Carbohydrate Chemistry, 2014, 33(4): 197-205.

DOI：10.1080/07328303.2014.907908

• Idurono-6
• 3-lactone
• X-ray crystal structure
• Chlorination

Attempted synthesis of the imidazylate derivative of 1,2-O-isopropylidene--D-glucurono-6,3-lactone (2) via treatment with sulfuryl chloride in the presence of excess imidazole in DMF at either -40 degrees C or -70 degrees C resulted in the unexpected formation of 5-chloro-5-deoxy-1,2-O-isopropylidene--l-idurono-6,3-lactone (7). Chloride 7 presumably forms via the rapid S(N)2 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.

• 出版日期2014-5-4