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Deoxygenation of carbohydrates by thiol-catalysed radical-chain redox rearrangement of the derived benzylidene acetals

✍ Scribed by Dang, Hai-Shan; Roberts, Brian P.; Sekhon, Jasmeet; Smits, Teika M.

Book ID: 120821076
Publisher: Royal Society of Chemistry
Year: 2003
Tongue: English
Weight: 249 KB
Volume: 1
Category: Article
ISSN: 1477-0520
DOI: 10.1039/B212303G

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Radical-chain redox rearrangement of cyclic benzylidene acetals to benzoate esters in the presence of thiols

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Cyclic benzylidene acetals derived from 1,2-and 1,3-diols undergo an efficient ring-opening redox rearrangement to give benzoate esters in the presence of a peroxide initiator and a thiol, which acts as a polarity-reversal catalyst to promote the radical-chain reaction.

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Regioselectivity in the ring opening of

Regioselectivity in the ring opening of 2-phenyl-1,3-dioxan-2-yl radicals derived from cyclic benzylidene acetals and comparison with deoxygenation of a carbohydrate diol via its cyclic thionocarbonate

✍ Brian P Roberts; Teika M Smits 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 107 KB

Ring-opening b-scission of monocyclic 2-phenyl-1,3-dioxan-2-yl radicals gives preferentially the more stabilised alkyl radical. However, analogous bicyclic radicals derived from two 4,6-O-benzylidene glucopyranosides afford primary radicals in preference to secondary radicals, a result that can be r