A Photo-Favorskii Ring Contraction Reaction: The Effect of Ring Size
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F13%3A00066104" target="_blank" >RIV/00216224:14310/13:00066104 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1021/jo300850a" target="_blank" >http://dx.doi.org/10.1021/jo300850a</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/jo300850a" target="_blank" >10.1021/jo300850a</a>
Alternative languages
Result language
angličtina
Original language name
A Photo-Favorskii Ring Contraction Reaction: The Effect of Ring Size
Original language description
The effect of ring size on the photo-Favorskii induced ring-contraction reaction of the hydroxybenzocycloalkanonyl acetate and mesylate esters (7a?d, 8a?c) has provided new insight into the mechanism of the rearrangement. By monotonically decreasing thering size in these cyclic derivatives, the increasing ring strain imposed on the formation of the elusive bicyclic spirocyclopropanone 20 results in a divergence away from rearrangement and toward solvolysis. Cycloalkanones of seven or eight carbons undergo a highly efficient photo-Favorskii rearrangement with ring contraction paralleling the photochemistry of p-hydroxyphenacyl esters. In contrast, the five-carbon ring does not rearrange but is diverted to the photosolvolysis channel avoiding the increased strain energy that would accompany the formation of the spirobicyclic ketone, the ?Favorskii intermediate 20?. The six-carbon analogue demonstrates the bifurcation in reaction channels, yielding a solvent-sensitive mixture of both.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach
Others
Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
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Volume of the periodical
78
Issue of the periodical within the volume
5
Country of publishing house
US - UNITED STATES
Number of pages
12
Pages from-to
1718-1729
UT code for WoS article
000315707500003
EID of the result in the Scopus database
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