About: A Photo-Favorskii Ring Contraction Reaction: The Effect of Ring Size

Facets (new session)
Description
Metadata
Settings
- owl:sameAs
- Inference Rule:

About: A Photo-Favorskii Ring Contraction Reaction: The Effect of Ring Size Goto Sponge NotDistinct Permalink

An Entity of Type : http://linked.opendata.cz/ontology/domain/vavai/Vysledek, within Data Space : linked.opendata.cz associated with source document(s)

Attributes	Values
rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
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 the ring 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. 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 the ring 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. (en)
Title	A Photo-Favorskii Ring Contraction Reaction: The Effect of Ring Size A Photo-Favorskii Ring Contraction Reaction: The Effect of Ring Size (en)
skos:prefLabel	A Photo-Favorskii Ring Contraction Reaction: The Effect of Ring Size A Photo-Favorskii Ring Contraction Reaction: The Effect of Ring Size (en)
skos:notation	RIV/00216224:14310/13:00066104!RIV14-MSM-14310___
http://linked.open...avai/riv/aktivita	P S
http://linked.open...avai/riv/aktivity	P(ED0001/01/01), P(GA203/09/0748), P(ME09021), S
http://linked.open...iv/cisloPeriodika	5
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Klán, Petr Šolomek, Tomáš Heger, Dominik Ngoy, Bokolombe Pitchou Kammath, Viju Balachandran
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Masarykova univerzita / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	58935
http://linked.open...ai/riv/idVysledku	RIV/00216224:14310/13:00066104
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Photochemistry; hydroxyphenacyl; ring contraction (en)
http://linked.open.../riv/klicoveSlovo	ring contraction hydroxyphenacyl Photochemistry
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[E65BE7EC04F8]
http://linked.open...i/riv/nazevZdroje	Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	5 (xsd:int)
http://linked.open...cetTvurcuVysledku	7 (xsd:int)
http://linked.open...vavai/riv/projekt	New photoactivatable compounds for organic chemistry and biology New photoactivatable systems for biological studies CETOCOEN
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	78
http://linked.open...iv/tvurceVysledku	Klán, Petr Heger, Dominik Šolomek, Tomáš Givens, Richard Ngoy, Bokolombe Pitchou Kammath, Viju Balachandran Rubina, Marina
http://linked.open...ain/vavai/riv/wos	000315707500003
issn	0022-3263
number of pages	12 (xsd:int)
http://bibframe.org/vocab/doi	10.1021/jo300850a
http://localhost/t...ganizacniJednotka	14310

Faceted Search & Find service v1.16.118 as of Jun 21 2024

Alternative Linked Data Documents: ODE Content Formats:

RDF

ODATA

Microdata

About

OpenLink Virtuoso version 07.20.3240 as of Jun 21 2024, on Linux (x86_64-pc-linux-gnu), Single-Server Edition (126 GB total memory, 67 GB memory in use)
Data on this page belongs to its respective rights holders.
Virtuoso Faceted Browser Copyright © 2009-2024 OpenLink Software