Skeletal Rearrangements Resulting from Reactions of 1,6:2,3- and 1,6:3,4-Dianhydro-beta-D-hexopyranoses with Diethylaminosulphur Trifluoride

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F12%3A00369111" target="_blank" >RIV/67985858:_____/12:00369111 - isvavai.cz</a>

Alternative codes found

RIV/00216208:11310/12:10127585

Result on the web

<a href="http://dx.doi.org/10.1039/c1ob06336g" target="_blank" >http://dx.doi.org/10.1039/c1ob06336g</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c1ob06336g" target="_blank" >10.1039/c1ob06336g</a>

Result language

angličtina

Original language name

Skeletal Rearrangements Resulting from Reactions of 1,6:2,3- and 1,6:3,4-Dianhydro-beta-D-hexopyranoses with Diethylaminosulphur Trifluoride

Original language description

A complete series of eight 1,6:2,3- and 1,6:3,4-dianhydro-beta-D-hexopyranoses were subjected to fluorination with DAST. The 1,6:3,4-dianhydropyranoses yielded solely products of skeletal rearrangement resulting from migration of the tetrahydropyran oxygen (educts of D-altro and D-talo configuration) or of the 1,6-anhydro bridge oxygen (D-allo, D-galacto). The major products yielded by the 1,6:2,3-dianhydropyranoses were compounds arising from nucleophilic substitution, with configuration at C4 either retained (D-talo, D-gulo) or inverted (D-manno), or from C6 migration (D-allo). The minor products in the 1,6:2,3-series resulted from migration of the tetrahydropyran oxygen (D-gulo) or the oxirane oxygen (D-manno), or from nucleophilic substitution withretention of configuration (D-manno). The structure of most of the rearranged products was verified by X-ray crystallography.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CF - Physical chemistry and theoretical chemistry

OECD FORD branch

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Project

<a href="/en/project/IAA400720706" target="_blank" >IAA400720706: Structure of silyl moieties through J(29Si-13C) couplings as determined by triple {1H, 13C}29Si NMR experiments</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2012

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Organic & Biomolecular Chemistry

ISSN

1477-0520

e-ISSN

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Volume of the periodical

10

Issue of the periodical within the volume

2

Country of publishing house

GB - UNITED KINGDOM

Number of pages

10

Pages from-to

394-403

UT code for WoS article

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EID of the result in the Scopus database

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