Tandem Staudinger/aza-Wittig reaction of 6-azido-6-deoxycellulose derivative

• Tandem Staudinger/aza-Wittig reaction of a 6-azidocellulose derivative.
• Conversion of 6-isothiocyanatocellulose to a crown ether-appended cellulose.
• One-pot synthesis of the crown ether-appended cellulose from the 6-azidocellulose.

The tandem Staudinger/aza-Wittig reaction of the 6-azido-6-deoxycellulose derivative (2) with triphenylphosphine and carbon disulfide afforded the corresponding 6-isothiocyanato-6-deoxycellulose derivative (3) in 47.3% yield. Compound 3 was further reacted with 4′-aminobenzo-15-crown ether to afford the crown ether-containing 6-N-thioureido-6-deoxycellulose derivative (4) in 70.0% yield. Compound 4 was also obtained in 28.7% yield from the one-pot reaction (tandem Staudinger/aza-Wittig reaction/thiocarbamoylation) of compound 2. The tandem Staudinger/aza-Wittig reaction is a useful alternative to the Huisgen reaction for the synthesis of functional cellulose derivatives from 6-azido-6-deoxycellulose derivatives.

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