title: Exclusive ring opening of gem-dihalo-1,2-cyclopropanated oxyglycal to oxepines in AgOAc.
abstract: Treatment of gem-dihalo-1,2-cyclopropanated d-oxyglycal with primary, secondary, and unsaturated alcohols, in the presence of AgOAc, leads to the formation of chloro-oxepines exclusively. Reaction of the resulting 2-chloro-oxepines with excess alcohol in the presence of AgOAc, do not promote further reactions. This result is in contrast to the reactions of d-glucal derived halo-oxepine with alcohols known previously that lead to the formation of furanoses as the major product under similar reaction conditions. Observation of this study consolidates the reactivity differences of gem-dihalo-1,2-cyclopropanated oxyglycals, as compared to gem-dihalo-1,2-cyclopropanated glycals.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
authors.forename: Supriya
authors.initials: S
authors.lastname: Dey
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India. Electronic address: jayaraman@orgchem.iisc.ernet.in.
authors.forename: N
authors.initials: N
authors.lastname: Jayaraman
mesh_terms: D000085:Acetates / Q000737:chemistry*; D002125:Calcium Gluconate / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry*; D010082:Oxepins / Q000737:chemistry*; D018030:Silver Compounds / Q000737:chemistry*
chemical_list: D000085:Acetates; D003521:Cyclopropanes; D010082:Oxepins; D018030:Silver Compounds; C103100:silver acetate; D002125:Calcium Gluconate
keywords: Cyclopropanes; Glycals; Oxepines; Oxyglycals; Ring expansion; Septanosides