Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F15%3A00088775" target="_blank" >RIV/00216224:14310/15:00088775 - isvavai.cz</a>
Result on the web
<a href="http://www.sciencedirect.com/science/article/pii/S0040403915300575" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0040403915300575</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tetlet.2015.09.015" target="_blank" >10.1016/j.tetlet.2015.09.015</a>

Result language
angličtina
Original language name
Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission
Original language description
alpha-Hydroxy-beta-dicarbonyls are known to undergo base-induced rearrangement to alpha-acyloxy carbonyls by a mechanism believed to involve an oxirane C-C bond scission step. Herein, we report the first example of this process in a vinylogous system. An attempt to access the protected form of the putative oxirane intermediate revealed an additional rearrangement pathway that was available to the substrate. Oxirane C-C bond cleavage mechanisms were invoked to explain both isomerizations. (C) 2015 Elsevier Ltd. All rights reserved.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
—

Project
<a href="/en/project/GJ15-10504Y" target="_blank" >GJ15-10504Y: Access to unique modulators of adenylyl cyclase</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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