title: Tandem Staudinger/aza-Wittig reaction of 6-azido-6-deoxycellulose derivative.
abstract: 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.
authors.affiliation: Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Kyoto, Japan.
authors.forename: Masaya
authors.initials: M
authors.lastname: Shibano
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Kamitakahara
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Takano
mesh_terms: D002482:Cellulose / Q000031:analogs & derivatives* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D043844:Crown Ethers / Q000737:chemistry; D017879:Isothiocyanates / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry
chemical_list: C000590804:6-azido-6-deoxycellulose; D043844:Crown Ethers; D017879:Isothiocyanates; D009943:Organophosphorus Compounds; C061896:triphenylphosphine; C037152:isothiocyanic acid; D002482:Cellulose
keywords: Cellulose isothiocyanate; Crown ether-appended cellulose; Isothiocyanation; N-Thioureido cellulose derivative