title: N-(tert-butoxycarbonyl)-N-[(triethylenediammonium)sulfonyl]azanide: a convenient sulfamoylation reagent for alcohols.
abstract: A convenient and efficient procedure is described for the sulfamoylation of alcohols using N-(tert-butoxycarbonyl)-N-[(triethylenediammonium)sulfonyl]azanide (1). The ambient temperature stable reagent 1 reacts with phenols as well as primary and secondary alcohols to give high to modest yields. The relative reaction rate of substrates was determined (primary > phenol > secondary ≫ tertiary). The reagent's utility as a selective sulfamoylation reagent with polyols is also demonstrated.
authors.affiliation: Millennium Pharmaceuticals, Inc. , Process Chemistry Research and Development, 35 Landsdowne Street, Cambridge, Massachusetts 02139, United States.
authors.forename: Ian
authors.initials: I
authors.lastname: Armitage
authors.forename: Alexander M
authors.initials: AM
authors.lastname: Berne
authors.forename: Eric L
authors.initials: EL
authors.lastname: Elliott
authors.forename: Mingkun
authors.initials: M
authors.lastname: Fu
authors.forename: Frederick
authors.initials: F
authors.lastname: Hicks
authors.forename: Quentin
authors.initials: Q
authors.lastname: McCubbin
authors.forename: Lei
authors.initials: L
authors.lastname: Zhu
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000588:Amines; D007202:Indicators and Reagents; D015394:Molecular Structure; D010636:Phenols; D013450:Sulfones / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000588:Amines; D007202:Indicators and Reagents; C587806:N-(tert-butoxycarbonyl)-N-((triethylenediammonium)sulfonyl)azanide; D010636:Phenols; D013450:Sulfones