Some special features of hydroalumination-iodination of alkyne-1,4-diols

Bobbitt’s Salt-Mediated Oxidation of Alkynyl-ols and -diols to the Corresponding Aldehydes and Their Application in Tandem Reactions

“…This was clearly observed in the 1 H NMR spectrum of the crude mixture by the appearance of proton signals in the aromatic region as well as the deshielded proton of the newly formed secondary alcohol (between 5 and 6 ppm). This alcohol was isolated by extraction with CH 2 Cl 2 but was not further purified before oxidation with Bobbitt’s salt to afford 1-phenylbut-2-yn-1-one ( 8 ) in 74% isolated yield following flash column chromatographic isolation (see the Supporting Information for details) . Ketone 8 is a useful building block in the preparation of covalent adaptable networks …”

“…This alcohol was isolated by extraction with CH 2 Cl 2 but was not further purified before oxidation with Bobbitt's salt to afford 1-phenylbut-2-yn-1-one (8) in 74% isolated yield following flash column chromatographic isolation (see the Supporting Information for details). 19 Ketone 8 is a useful building block in the preparation of covalent adaptable networks. 20 Subjecting a solution of aldehyde 3c (made by oxidation of 2c) to a Wittig reaction with a dibromomethylene ylide formed the Corey−Fuchs 1,1-dibromoolefin 9.…”