title: Ring-opening reactions of 2-alkoxy-3,4-dihydropyrans with thiols or thiophenols.
abstract: An electrophilic ring-opening reaction of 2-alkoxy-3,4-dihydropyran with a thiophenol or thiol is developed for the first time. The generated product contains not only a 1,3-dicarbonyl moiety but also a fragment of bis(alkylthio)methane. A possible mechanism is also proposed on the basis of postulating a ring-opening monotransthioacetalization product, which was prepared by using LiBr as catalyst as an intermediate.
authors.affiliation: Institute of Physical Chemistry and Industrial Catalysis, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Hongshan District, Wuhan, China.
authors.forename: Minghao
authors.initials: M
authors.lastname: Li
authors.forename: Haoquan
authors.initials: H
authors.lastname: Li
authors.forename: Tao
authors.initials: T
authors.lastname: Li
authors.forename: Yanlong
authors.initials: Y
authors.lastname: Gu
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D007659:Ketones; D010636:Phenols; D011714:Pyrans; D013438:Sulfhydryl Compounds; C042983:thiophenol; D008697:Methane