Edward Mc Nelis

Concerning the formations of α-iodoenones

Abstract The formations of α-iodoenones from secondary alkynols with NIS/HTIB (cat.), tertiary alkynols with I 2 /PDC and enones with I 2 /pyridine have been compared. In the latter two reactions the PDC and the pyridine have been found to be catalytic.

Furo[3,4-b]furan formations from alkynols of xylose

Abstract Treatment of iodoalkynol derivatives of xylose with iodonium-producing reagents afforded β,β-diiodoenol ethers contained in furo[3,4-b]furan cores.

Formations of α-Iodoenones by Iodine and Catalytic Amounts of Amines

Abstract Iodine and catalytic amounts of amines in a variety of solvents react with cyclic and acyclic enones to afford the corresponding α-iodoenones.

Ring expansions of 1-Haloethynyl-2-methylcyclopentanols

Abstract 1-Haloethynyl-2-methylcyclopentanols treated with iodine and HTIB ring expand stereoselectively depending on the relative position of the methyl and the hydroxyl groups. The products are 2-(dihalomethylidene)-3-methylcyclohexanones if the methyls are cis to the hydroxyl groups or 2-(dihalomethylidene)-6-methylcyclohexanones if the methyls are trans to the hydroxyls.

Ring Expansions of 2-Haloethynyl-2-norbornanols

2-Haloethynyl-2-norbornanols react with iodine and Kosers reagent in acetonitrile to afford two ring-expanded products, 2-[(Z)-haloiodomethylidene]bicyclo[3.2.1]octan-3-one and 3-[(Z)-haloiodomethylidene]bicyclo[3.2.1]octan-2-one. These results contrast with the 2-haloethynyl-2-bornanols which lead to the corresponding 3-octanones.

Formation of A Dihaloenone of Homoadamantanone

Abstract Adamantanone is converted to a (Z)-bromoiodomethylidene homoadamantanone via a sequence involving ethynyl Grignard addition, conversion to a bromoalkynol and treatment with iodine and [hydroxy(tosyloxy)iodo]benzene.

A new approach to the functionalization of phenanthrenequinone

Abstract The bromoethynyl adduct of fluorenone was converted to 10-((Z)-bromoiodomethylidene)phenanthren-9-one by means of the iodonium-generating reagent, iodine and Kosers reagent.

Ring halogenations of polyalkylbenzenes by ionic halides and Koser's reagent

Abstract Ring chlorinations of polyalkylbenzenes such as mesitylene have been carried out at room temperature with LiCl or NaCl and stoichiometric amounts of Kosers reagent. Solvents range from water to methylene chloride. The procedures were extended to bromination and iodination.

Conversions of phenylalkynylcyclopentanols to α-iodoenones

Abstract N-Iodosuccinimide and catalytic amounts of Kosers reagent react with phenylalkynyleyclopentanols to afford α-iodoenones. No ring expansions occur.

Comparison of Iodonium-Producing Reagents in the Shift Reaction of A Bromopropynyl Alcohol

Abstract A variety of iodonium-producing reagents have been compared for synthetic utility in the shift reaction of bromopropynyl alcohol 1 to dihaloene 2. The combinations of I2/HTIB, I2/I2O5 and NIS/TsOH were found to afford excellent yields.