Methylene Acetal Formation from 1,2- and 1,3-Diols Using an O,S-Acetal, 1,3-Dibromo-5,5-dimethylhydantoin, and BHT

Abstract

A mild and efficient method for formation of methylene acetals from 1,2- and 1,3-diols using methoxymethylphenylsulfide, 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), and dibutylhydroxytoluene (BHT) is described. The use of BHT in this process suppresses side reactions and enables high-yielding formation of methylene acetals of various diols, including carbohydrate-type substrates.

Azidomethylation of Nucleobases and Related N-Heterocycles, Benzazoles, and Bis(arene)sulfonimides Using Azidomethyl Esters with Silyl Triflates

“…Furthermore, this chemistry could be applied to the combination of azidomethyl phenyl sulfide (4, 1.0 equiv) and 1,3-dibromo-5,5-dimethylhydantoin (DBDMH, 1.5 equiv), and the azidomethylation of 2a at 80 °C afforded 3a in 62% yield (Scheme 4). 13 This reaction proceeds via the oxidation of the sulfur center in 4 by DBDMH, an electrophilic bromonium ion source, to generate the corresponding azidomethylium species in situ. This result strongly supported the formation of azidomethylium species through two electrons from the nitrogen atom of the azide group flowing toward the carbon atom as described above.…”

Practical Glucosylations and Mannosylations Using Anomeric Benzoyloxy as a Leaving Group Activated by Sulfonium Ion

“…Commercially available reagents were used without further purification. The starting materials 1a , 1c–1o , − 2c , 2f , 2g , 2h , 2n–2o, and MeSCH 2 Cl were prepared according to the literature. 1 H NMR and 13 C NMR spectra were recorded with a 400 or 600 MHz spectrometer using tetramethylsilane (TMS) as an internal standard.…”

Syntheses of Bromo-N-heterocycles through Dibromohydantoin-Promoted Tandem C–H Amination/Bromination

“…Thus, we became interested in devising as yet unprecedented synthesis of bromo- N -heterocycles through intramolecular tandem C–H amination and bromination. Through our endeavor, various bromo- N -heterocycles were obtained with dibromohydantoin (DBH) as both the amination and bromination reagents and water as the major solvent.…”