title: Direct synthesis of anti-1,3-diols through nonclassical reaction of aryl Grignard reagents with isopropenyl acetate.
abstract: A series of symmetrical aromatic 1,3-diols were efficiently synthesized from substituted aryl Grignard reagents and isopropenyl acetate in a one-step reaction that formed anti products as the major species. Both experimental and theoretical studies suggested that the reaction involves the formation of a relatively stable intermediate E containing a six-membered ring from intermediate A. The stereoselectivity of the reactions and the molecular structure of the products were confirmed by NMR spectroscopy, X-ray diffraction, and gas chromatography.
authors.affiliation: School of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China.
authors.forename: Yinchun
authors.initials: Y
authors.lastname: Jiao
authors.forename: Chenzhong
authors.initials: C
authors.lastname: Cao
authors.forename: Zaichun
authors.initials: Z
authors.lastname: Zhou
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D000085:Acetates; D000438:Alcohols; D007202:Indicators and Reagents; C555950:isopropenyl acetate